Aromatic amine derivatives and organic electroluminescent elements using same

ABSTRACT

Provided are an organic EL device material that reduce the driving voltage of an organic EL device and increase the lifetime of the device as compared with a conventional organic EL device material. Also provided are organic electroluminescence devices containing the organic EL device material.

TECHNICAL FIELD

The present invention relates to an aromatic amine derivative and anorganic electroluminescence (organic EL) device using the same.

BACKGROUND ART

An organic EL device is a spontaneous light emitting device whichutilizes such a principle that a fluorescent substance emits light byvirtue of recombination energy of holes injected from an anode andelectrons injected from a cathode by an application of an electricfield. Since an organic EL device of the laminate type capable of beingdriven under low electric voltage has been reported by C. W. Tang et al.of Eastman Kodak Company (see Non Patent Literature 1), many studieshave been conducted for an organic EL device using an organic materialas a constituent material.

Tang et al. discloses an organic EL device having a laminate structurein which tris(8-quinolinolato)aluminum is used in a light emitting layerand a triphenyldiamine derivative is used in a hole transporting layer.Advantages of adopting the laminate structure in the organic EL deviceinclude: (i) injection efficiency of holes into the light emitting layercan be increased; (ii) efficiency of forming excitons which are formedthrough recombination in the light emitting layer can be increased byblocking electrons injected from the cathode toward the light emittinglayer in the hole transporting (injecting) layer; and (iii) excitonsformed in the light emitting layer can be easily enclosed in the lightemitting layer. In order to increase the efficiency of recombination ofinjected holes and electrons in the organic EL device having suchlaminate structure, there have been made refinements of the devicestructure and a method of forming the device, and studies on a materialitself for each layer.

In general, when an organic EL device is driven or stored in anenvironment of high temperature, there occur adverse affects such as achange in luminescent color, a decrease in luminous efficiency, anincrease in driving voltage, and a decrease in lifetime of lightemission.

In order to prevent such adverse effects, there have been reported, ashole transporting material, aromatic amine derivatives each having acarbazole skeleton (see Patent Literatures 1 to 3), an aromatic aminederivative having a dibenzofuran skeleton or a dibenzothiophene skeletonand a fluorene skeleton (see Patent Literature 4), and the like.

CITATION LIST Patent Literature

-   [PTL 1] WO 07/148,660 A1-   [PTL 2] WO 08/062,636 A1-   [PTL 3] US 2007-0215889 A1-   [PTL 4] JP 2005-290000 A Non Patent Literature-   [NPL 1] C. W. Tang, S. A. Vanslyke, “Applied Physics Letters,” Vol.    51, p. 913, 1987

SUMMARY OF INVENTION Technical Problem

However, the aromatic amine derivatives disclosed in Patent Literatures1 to 4 are still susceptible to improvement because it cannot be saidthat a reduction in the driving voltage of a device and the lifetime ofthe device are satisfactory.

In view of the foregoing, an object of the present invention is toprovide an organic EL device material capable of reducing the drivingvoltage of an organic EL device and increasing the lifetime of thedevice as compared with a conventional organic EL device material, andan organic EL device using the material.

Solution to Problem

The inventors of the present invention have made extensive studies toachieve the object, and as a result, have found the following. When anaromatic amine derivative having a fluorene skeleton and a carbazoleskeleton, a dibenzofuran skeleton, or a dibenzothiophene skeleton isused as a material for an organic EL device, in particular, a holetransporting material, an additional reduction in the driving voltage ofthe organic EL device is achieved because of its high charge mobility.In addition, the stability of a thin film is improved, and henceadditional lengthening of the lifetime of the organic EL device isachieved.

That is, the present invention relates to the following items (1) and(2).

(1) An aromatic amine derivative represented by the following formula(I):

in the formula (I), Ar^(a) is represented by the following formula (II):

in the formula (II):

L^(a) represents a single bond, or a substituted or unsubstitutedarylene group having 6 to 50 ring carbon atoms;

R¹ and R² each represent a linear or branched alkyl group having 1 to 50carbon atoms, or an aryl group having 6 to 50 ring carbon atoms;

R³ and R⁴ each independently represent a linear or branched alkyl grouphaving 1 to 50 carbon atoms, a linear or branched alkenyl group having 3to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms,an aryl group having 6 to 50 ring carbon atoms, a heteroaryl grouphaving 5 to 50 ring atoms, a triarylalkyl group having aryl groups eachhaving 6 to 50 ring carbon atoms, a trialkylsilyl group having alkylgroups each having 1 to 50 carbon atoms, a triarylsilyl group havingaryl groups each having 6 to 50 ring carbon atoms, an alkylarylsilylgroup having an alkyl group having 1 to 50 carbon atoms and an arylgroup having 6 to 50 ring carbon atoms, a halogen atom, or a cyanogroup, and a plurality of R³'s or R⁴'s adjacent to each other, or R³ andR⁴ may be bonded to each other to form a ring; and

o represents an integer of 0 to 3 and p represents an integer of 0 to 4;

in the formula (I), Ar^(b) is represented by the following formula(III):

in the formula (III):

X represents NR^(a), an oxygen atom, or a sulfur atom, and R^(a)represents a substituted or unsubstituted aryl group having 6 to 50 ringcarbon atoms, or a triarylalkyl group having substituted orunsubstituted aryl groups each having 6 to 50 ring carbon atoms;

R⁵, R⁶, and R⁷ each independently represent a linear or branched alkylgroup having 1 to 50 carbon atoms, a linear or branched alkenyl grouphaving 3 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ringcarbon atoms, an aryl group having 6 to 50 ring carbon atoms, aheteroaryl group having 6 to 50 ring atoms, a triarylalkyl group havingaryl groups each having 6 to 50 ring carbon atoms, a trialkylsilyl grouphaving alkyl groups each having 1 to 50 carbon atoms, a triarylsilylgroup having aryl groups each having 6 to 50 ring carbon atoms, analkylarylsilyl group having an alkyl group having 1 to 50 carbon atomsand an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or acyano group, and a plurality of R⁵'s, R⁶'s, or R⁷'s adjacent to eachother, or R⁵ and R⁶ may be bonded to each other to form a ring;

n represents an integer of 2 to 4 when X represents NR^(a), andrepresents an integer of 0 to 4 when X represents an oxygen atom or asulfur atom;

when n represents an integer of 2 to 4, R⁷'s on different benzene ringsmay be identical to or different from each other, and respective R⁷'spresent on benzene rings adjacent to each other may be bonded to eachother to form a ring; and

q represents an integer of 0 to 3, r and s each independently representan integer of 0 to 4, and when n represents an integer of 2 to 4, s'sthat specify the numbers of R⁷'s on different benzene rings may have thesame value or may have different values; and in the formula (I), Ar^(c)represents a substituted or unsubstituted aryl group having 6 to 50 ringcarbon atoms, or is represented by the formula (III).

(2) An organic electroluminescence device, including one or more organicthin-film layers including at least a light emitting layer, the organicthin-film layers being interposed between an anode and a cathode, inwhich at least one layer of the organic thin-film layers contains thearomatic amine derivative according to the above-mentioned item (1).

Advantageous Effects of Invention

When the aromatic amine derivative of the present invention is used as amaterial for an organic EL device, the driving voltage of the organic ELdevice can be reduced because of its high charge mobility. In addition,the stability of a thin film is improved, and hence the lifetime of theorganic EL device is additionally lengthened.

DESCRIPTION OF EMBODIMENTS

An aromatic amine derivative of the present invention is an aromaticmonoamine derivative represented by the following formula (I).

In the formula (I), Ar^(a) is represented by the following formula (II).

In the formula (II), L^(a) represents a single bond, or a substituted orunsubstituted arylene group having 6 to 50 ring carbon atoms. Examplesof the arylene group include a phenylene group, a biphenylene group, aterphenylene group, a naphthylene group, an acenaphthylenylene group, ananthranylene group, a phenanthrenylene group, apyrenylene group, anaphthacenylene group, a quaterphenylene group, a pentacenylene group, aperylenylene group, a coronylene group, a fluorenylene group, a9,9-dimethylfluorenylene group, an acenaphthofluorenylene group, ans-indacenylene group, an as-indacenylene group, and a chrycenylenegroup. The arylene group is preferably an arylene group having 6 to 24ring carbon atoms, more preferably a phenylene group, a biphenylenegroup, a terphenylene group, a phenanthrenylene group, a quaterphenylenegroup, or a fluorenylene group, still more preferably a phenylene group,a biphenylene group, a terphenylene group, or a quaterphenylene group,particularly preferably a p-phenylene group, a p-biphenylene group, ap-terphenylene group, or a p-quaterphenylene group. When a benzene ringis bonded at a para position, the driving voltage of a device isreduced. This is probably because a charge mobility is increased by theexpansion of a conjugated system. When the benzene ring is bonded at ameta position, the luminous efficiency of the device is improved. Thisis probably because the energy gap of a hole transporting layerincreases.

In addition, the arylene group represented by La may have a substituent,and examples of the substituent include: alkyl groups each having 1 to10 (preferably 1 to 6) carbon atoms such as a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, an s-butyl group, a t-butyl group, various pentylgroups, and various hexyl groups; cycloalkyl groups each having 3 to 10(preferably 5 to 7) ring carbon atoms such as a cyclopropyl group, acyclopentyl group, a cyclohexyl group, a cyclooctyl group, and acyclodecyl group; trialkylsilyl groups each having alkyl groups eachhaving 1 to 10 (preferably 1 to 6) carbon atoms such as a trimethylsilylgroup and a triethylsilyl group; triarylsilyl groups each having arylgroups each having 6 to 20 (preferably 6 to 10) ring carbon atoms suchas a triphenylsilyl group; alkylarylsilyl groups each having an alkylgroup having 1 to 10 (preferably 1 to 6) carbon atoms and an aryl grouphaving 6 to 20 (preferably 6 to 10) ring carbon atoms; halogen atomssuch as a fluorine atom, a chlorine atom, a bromine atom, and an iodineatom; and a cyano group (hereinafter, these groups are referred to as“substituents A”).

L^(a) represents preferably a single bond or a phenylene group, morepreferably a single bond. When L^(a) represents a single bond, thefluorene skeleton is directly bonded to the nitrogen atom. Accordingly,it is conceivable that an ionization potential reduces, and holes areaccumulated at an interface between the hole transporting layer and alight emitting layer to promote the injection of electrons. Thus, thedriving voltage of the organic EL device is additionally reduced.

In the formula (II), R¹ and R² each represent a linear or branched alkylgroup having 1 to 50 carbon atoms, or an aryl group having 6 to 50 ringcarbon atoms.

Examples of the alkyl group represented by each of R¹ and R² include amethyl group, an ethyl group, an n-propyl group, an isopropyl group, ann-butyl group, an isobutyl group, an s-butyl group, a t-butyl group,various pentyl groups (the term “various” means that a linear group andall kinds of branched groups are included, and the same holds true forthe following), various hexyl groups, various heptyl groups, variousoctyl groups, various nonyl groups, various decyl groups, variousundecyl groups, and various dodecyl groups. When the alkyl chain of thealkyl group is elongated, the aromatic amine derivative of the presentinvention can be suitably used in the production of the organic ELdevice by an application method because its solubility is improved. Thealkyl group suitable for the application method is preferably an alkylgroup having 1 to carbon atoms, more preferably an alkyl group having 1to 10 carbon atoms, still more preferably an alkyl group having 1 to 8carbon atoms. In addition, when the alkyl group has 5 or less carbonatoms, the aromatic amine derivative of the present invention can besuitably used in the production of the organic EL device by a depositionmethod because its molecular weight can be suppressed. The alkyl groupsuitable for the deposition method is preferably an alkyl group having 1to 5 carbon atoms, more preferably an alkyl group having 1 to 3 carbonatoms, still more preferably a methyl group.

Examples of the aryl group represented by each of R¹ and R² include aphenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylylgroup, a biphenylenyl group, a naphthyl group, a phenylnaphthyl group,an acenaphthylenyl group, an anthryl group, a benzanthryl group, anaceanthryl group, a phenanthryl group, a benzophenanthryl group, aphenalenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a7-phenyl-9,9-dimethylfluorenyl group, a pentacenyl group, a picenylgroup, a pentaphenyl group, pyrenyl group, a chrysenyl group, abenzochrysenyl group, an s-indacenyl group, an as-indacenyl group,fluoranthenyl group, and perylenyl group. The aryl group is preferablyan aryl group having 6 to 20 ring carbon atoms, more preferably and arylgroup having 6 to 14 ring carbon atoms, more preferably an aryl grouphaving 6 to 10 ring carbon atoms, still more preferably a phenyl group.

Of those, a methyl group or a phenyl group is preferred as each of R¹and R². In particular, in the case where R¹ and R² each represent analkyl group having 1 to 10 carbon atoms, the molecular weight becomessmall as compared with that in the case where R¹ and R² each representan aryl group. Accordingly, a deposition temperature is easily adjustedto fall within a proper range, and hence the thermal decomposition ofthe material can be prevented. Accordingly, R¹ and R² each morepreferably represent a methyl group.

In the formula (II), R³ and R⁴ each independently represent a linear orbranched alkyl group having 1 to 50 carbon atoms, a linear or branchedalkenyl group having 3 to 50 carbon atoms, a cycloalkyl group having 3to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms,a heteroaryl group having to 50 ring atoms, a triarylalkyl group havingaryl groups each having 6 to 50 ring carbon atoms, a trialkylsilyl grouphaving alkyl groups each having 1 to 50 carbon atoms, a triarylsilylgroup having aryl groups each having 6 to 50 ring carbon atoms, analkylarylsilyl group having an alkyl group having 1 to 50 carbon atomsand an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or acyano group.

Examples of the alkyl group and the aryl group each represented by eachof R³ and R⁴ include the same examples as those of R¹ and R², andpreferred examples thereof are also the same. It should be noted thatthe alkyl group may be substituted with a hydroxyl group and the arylgroup may be substituted with an alkyl group having 1 to 10 (preferably1 to 5) carbon atoms or a cycloalkyl group having 3 to 10 ring carbonatoms.

Examples of the alkenyl group represented by each of R³ and R⁴ includegroups each obtained by making at least one carbon-carbon bond in agroup having 2 to 50 carbon atoms out of the alkyl groups represented byR³ and R⁴ a double bond.

Examples of the cycloalkyl group represented by each of R³ and R⁴include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, acyclooctyl group, a cyclodecyl group, a cylopentylmethyl group, acylohexylmethyl group, a cyclohexylethyl group, a 1-adamantyl group, a2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group. Ofthose, a cycloalkyl group having 3 to ring carbon atoms is preferred, acycloalkyl group having 3 to ring carbon atoms is more preferred, acycloalkyl group having 3 to 6 ring carbon atoms is still morepreferred, and a cyclopentyl group or a cyclohexyl group is stillfurther more preferred. The cycloalkyl group may be substituted with ahalogen atom such as a fluorine atom, a chlorine atom, a bromine atom,or an iodine atom (preferably a fluorine atom).

Examples of the heteroaryl group represented by each of R³ and R⁴include groups each obtained by substituting at least one carbon atom inthe aryl group represented by each of R³ and R⁴ with a nitrogen atom oran oxygen atom. The heteroaryl group may be substituted with an alkylgroup having 1 to 10 (preferably 1 to 5) carbon atoms or a cycloalkylgroup having 3 to 10 ring carbon atoms.

Examples of the aryl groups and the alkyl group in the triarylalkylgroup represented by each of R³ and R⁴ include the same examples asthose of the aryl group and the alkyl group each represented by each ofR³ and R⁴. Preferred examples thereof are also the same, and examples ofthe substituent which any such group may have also include the sameexamples. The triarylalkyl group is preferably a triphenylmethyl groupor a trinaphthylmethyl group, more preferably a triphenylmethyl group.The three aryl groups with which the alkyl group is substituted may beidentical to or different from one another.

Examples of the alkyl groups in the trialkylsilyl group represented byeach of R³ and R⁴ include the same examples as those of the alkyl grouprepresented by each of R³ and R⁴. Preferred examples thereof are alsothe same, and examples of the substituent which any such group may havealso include the same examples. The three alkyl groups with which thesilyl group is substituted may be identical to or different from oneanother.

Examples of the aryl groups in the triarylsilyl group represented byeach of R³ and R⁴ include the same examples as those of the aryl grouprepresented by each of R³ and R⁴. Preferred examples thereof are alsothe same, and examples of the substituent which any such group may havealso include the same examples. Of those, a triphenylsilyl group or atrinaphthylsilyl group is preferred as the triarylsilyl group, and atriphenylsilyl group is more preferred. The three aryl groups with whichthe silyl group is substituted may be identical to or different from oneanother.

Examples of the alkyl group and the aryl group in the alkylarylsilylgroup represented by each of R³ and R⁴ include the same examples asthose of the alkyl group and the aryl group each represented by each ofR³ and R⁴. Examples of the alkylarylsilyl group include amonoalkyldiarylsilyl group and a dialkylmonoarylsilyl group.

Examples of the halogen atom represented by each of R³ and R⁴ include afluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In addition, a plurality of R³'s or R⁴'s adjacent to each other, or R³and R⁴ may be bonded to each other to form a ring. The ring ispreferably formed of two R³'s or R⁴'s adjacent to each other, andexamples of the ring include a benzene ring and a naphthalene ring.

Of those, an aryl group having 6 to 50 ring carbon atoms, a triarylalkylgroup having aryl groups each having 6 to 50 ring carbon atoms, or atriarylsilyl group having aryl groups each having 6 to 50 ring carbonatoms is preferred as each of R³ and R⁴, and a phenyl group, atriphenylmethyl group, or a triphenylsilyl group is more preferred. Inaddition, a plurality of R³'s or R⁴'s adjacent to each other arepreferably bonded to each other to form a ring (more preferably abenzene ring).

When a plurality of R³'s or R⁴'s adjacent to each other, or R³ and R⁴are bonded to each other to form a ring, specific examples of thestructure of Ar^(a) include, but not particularly limited to, thefollowing structures.

In the formula (II), o represents an integer of 0 to 3, preferably 0 or1, more preferably 0, and p represents an integer of 0 to 4, preferably0 or 1.

It should be noted that when there exist a plurality of R³'s or R⁴'s,the plurality of R³'s or R⁴'s may be identical to or different from eachother. When R³ and R⁴ are placed at the 2- and 7-positions of thefluorene ring in the formula (II), such an effect that a site having ahigh electron density and rich in reactivity is protected may beexerted. Accordingly, the material becomes electrochemically stable, andhence the lifetime of the device is lengthened.

Of the formulae (II), the following formula (II′) in which the bondingposition of L^(a) is limited is preferred from the viewpoints of anadditionally high charge mobility and an additional reduction in thedriving voltage of the organic EL device.

In the formula (II′), L^(a), R¹, R², R³, R⁴, o, and p are as defined inthe foregoing.

Here, specific examples of Ar^(a) are shown below. However, Ar^(a) isnot particularly limited to these examples. It should be noted that awave dash represents a bonding site.

In addition, Ar^(b) in the formula (I) is represented by the followingformula (III).

X represents NR^(a), an oxygen atom, or a sulfur atom. R^(a) in NR^(a)represents a substituted or unsubstituted aryl group having 6 to 50 ringcarbon atoms, or a triarylalkyl group having substituted orunsubstituted aryl groups each having 6 to 50 ring carbon atoms. When Xrepresents NR^(a), an oxygen atom, or a sulfur atom, the charge mobilityis increased, and hence the voltage is reduced. In particular, when Xrepresents NR^(a), the driving voltage of the organic EL device isadditionally reduced, and when X represents an oxygen atom or a sulfuratom (especially an oxygen atom), resistance to reduction is improved,and hence the lifetime of the organic EL device is additionallylengthened.

Examples of the aryl group represented by R^(a) include the sameexamples as those of R¹ and R², and the aryl group is preferably an arylgroup having 6 to 20 ring carbon atoms, more preferably an aryl grouphaving 6 to 14 ring carbon atoms, still more preferably a phenyl groupor a naphthyl group. The aryl group may have a substituent, and examplesof the substituent include the substituents A. Of those, a triarylsilylgroup is preferred and a triphenylsilyl group is more preferred.

Examples of the aryl groups in the triarylalkyl group include the sameexamples as those of R¹ and R², and preferred examples thereof are alsothe same. Examples of the triarylalkyl group include a triphenylmethylgroup and a 2-triphenylethyl group. Of those, a triphenylmethyl group ispreferred.

In the formula (III), R⁵, R⁶, and R⁷ each independently represent alinear or branched alkyl group having 1 to 50 carbon atoms, a linear orbranched alkenyl group having 3 to 50 carbon atoms, a cycloalkyl grouphaving 3 to 50 ring carbon atoms, an aryl group having 6 to 50 ringcarbon atoms, a heteroaryl group having 6 to 50 ring atoms, atriarylalkyl group having aryl groups each having 6 to 50 ring carbonatoms, a trialkylsilyl group having alkyl groups each having 1 to 50carbon atoms, a triarylsilyl group having aryl groups each having 6 to50 ring carbon atoms, an alkylarylsilyl group having an alkyl grouphaving 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbonatoms, a halogen atom, or a cyano group.

Examples of each of the alkyl group, the alkenyl group, the cycloalkylgroup, the aryl group, the heteroaryl group, the triarylalkyl group, thetrialkylsilyl group, the triarylsilyl group, the alkylarylsilyl group,and the halogen atom include the same examples as those of R³ and R⁴,and preferred examples thereof are also the same. Further, examples ofthe substituent which each of the groups may have are the same.

In addition, a plurality of R⁵'s, R⁶'s, or R⁷'s adjacent to each other,or R⁵ and R⁶ may be bonded to each other to form a ring. The ring ispreferably formed of two R⁵'s or R⁶'s adjacent to each other, andexamples of the ring include a benzene ring and a naphthalene ring.

Of those, an aryl group having 6 to 50 ring carbon atoms is preferred aseach of R⁵ and R⁶, an aryl group having 6 to 20 ring carbon atoms ismore preferred, an aryl group having 6 to 10 ring carbon atoms is stillmore preferred, and a phenyl group is still further more preferred. Inaddition, a plurality of R⁵'s or R⁶'s adjacent to each other arepreferably bonded to each other to form a ring (more preferably abenzene ring). In addition, as for R⁷, a plurality of R⁷'s adjacent toeach other on the same benzene ring are preferably bonded to each otherto form a ring (more preferably a benzene ring).

It should be noted that when a plurality of R⁵'s or R⁶'s adjacent toeach other, or R⁵ and R⁶ are bonded to each other to form a ring,specific examples of the structure of Ar^(b) include, but notparticularly limited to, the following structures (in the formulae, R⁷,X, n, and s are as defined in the foregoing).

In the formula (III), n represents an integer of 2 to 4 when Xrepresents NR^(a), and represents an integer of 0 to 4 when X representsan oxygen atom or a sulfur atom.

When n represents an integer of 2 to 4, R⁷'s on different benzene ringsmay be identical to or different from each other. In addition,respective R⁷'s present on benzene rings adjacent to each other may bebonded to each other to form a ring, or as described in the foregoing,R⁷'s on the same benzene ring may be bonded to each other to form aring.

q represents an integer of 0 to 3, and r and s each independentlyrepresent an integer of 0 to 4. When q represents 2 or 3, a plurality ofR⁵'s may be identical to or different from each other. In addition, whenr represents an integer of 2 to 4, a plurality of R⁶'s may be identicalto or different from each other.

When n represents an integer of 2 to 4, s's that specify the numbers ofR⁷'s on different benzene rings may have the same value or may havedifferent values.

When R⁵ and R⁶ are placed preferably at the 3- and 6-positions, or 1-and 8-positions, of the heterocycle in the formula (III), morepreferably at the 3- and 6-positions, such an effect that a site havinga high electron density and rich in reactivity is protected is exerted.Accordingly, the material may become electrochemically stable, and hencethe lifetime of the organic EL device is lengthened.

Here, the following linking group in the formula (III) is referred to as“linking group B.”

(In the formula, R⁷, n, and s are as defined in the foregoing.)

When R⁷'s present on benzene rings adjacent to each other in the linkinggroup B or R⁷'s present on the same benzene ring are bonded to eachother to form a ring, specific examples of the structure of the linkinggroup B include, but not particularly limited to, the followingstructures.

When R⁷'s in the linking group B are bonded to each other to form aring, in other words, when the linking group B has no crosslink, thearomatic amine derivative of the present invention has such an effectthat an increase in the electron density of the compound is suppressedand its ionization potential is increased as compared with aconventional aromatic amine derivative.

As described later, when the linking group B is bonded to a paraposition with respect to X, such effect that an increase in the electrondensity of the compound is suppressed and its ionization potential isincreased is additionally enhanced.

In addition, when abenzene ring is bonded at the para position, thedriving voltage of the organic EL device is reduced. This is probablybecause the charge mobility is increased by the expansion of aconjugated system.

Of the formulae (III), the following formula (III′) in which the bondingposition of the linking group B is limited is preferred from theviewpoints of the suppression of an increase in the electron density ofthe compound, the increase of the ionization potential, and anadditional reduction in the driving voltage of the organic EL device.

In the formula (III′), X, R⁵, R⁶, R⁷, n, q, r, and s are as defined inthe foregoing.

Further, Ar^(b) is more preferably represented by any one of thefollowing formulae (III-1) to (III-6) out of the formulae (III) from theviewpoint of an additional reduction in the driving voltage of theorganic EL device.

In the formulae (III-1) to (III-6), R⁵, R⁶, R⁷, X, q, r, and s are asdefined in the foregoing, and R⁷'s or s's described in plurality may beidentical to or different from each other.

Ar^(b) is still more preferably represented by any one of the formulae(III-2), (III-3), and (III-6) out of the formulae (III-1) to (III-6).

Here, specific examples of Ar^(b) are shown below. However, Ar^(b) isnot particularly limited to these examples. It should be noted that awave dash represents a bonding site.

In addition, in the formula (I), Ar^(c) represents a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms, or isrepresented by the formula (III) (the formula (III′) and the formulae(III-1) to (III-6) are included, and the same holds true for thefollowing).

Examples of the aryl group represented by Ar^(c) include the sameexamples as those of R¹ and R², and a group represented by the formula(II) (the formula (II′) is included and the same holds true for thefollowing). Preferred examples of the aryl group include a phenyl group,a naphthylphenyl group, a biphenylyl group, a terphenylyl group, abiphenylenyl group, a naphthyl group, a phenylnaphthyl group, anacenaphthylenyl group, an anthryl group, a benzanthryl group, anaceanthryl group, a phenanthryl group, a benzophenanthryl group, aphenalenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a7-phenyl-9,9-dimethylfluorenyl group, a pentacenyl group, a picenylgroup, a pentaphenyl group, a pyrenyl group, a chrysenyl group, abenzochrysenyl group, an s-indacenyl group, an as-indacenyl group, afluoranthenyl group, a perylenyl group, and the group represented by theformula (II).

The aryl group may have a substituent, and the substituent is a groupselected from the group consisting of a linear or branched alkyl grouphaving 1 to 50 carbon atoms (preferably 1 to 10 carbon atoms, morepreferably 1 to 5 carbon atoms), a cycloalkyl group having 3 to 50carbon atoms (preferably 3 to 6 carbon atoms, more preferably 5 or 6carbon atoms), a trialkylsilyl group having alkyl groups each having 1to 50 carbon atoms (preferably 1 to 10 carbon atoms, more preferably 1to 5 carbon atoms), a triarylsilyl group having aryl groups each having6 to 50 ring carbon atoms (preferably 6 to 24 ring carbon atoms, morepreferably 6 to 12 ring carbon atoms), an alkylarylsilyl group having analkyl group having 1 to 50 carbon atoms (preferably 1 to 10 carbonatoms, more preferably 1 to 5 carbon atoms) and an aryl group having 6to 50 ring carbon atoms (preferably 6 to 24 ring carbon atoms, morepreferably 6 to 12 ring carbon atoms), a triarylalkyl group having arylgroups each having 6 to 50 ring carbon atoms (preferably 6 to 24 ringcarbon atoms, more preferably 6 to 12 ring carbon atoms), an aryl grouphaving 6 to 50 ring carbon atoms (preferably 6 to 24 ring carbon atoms,more preferably 6 to 12 ring carbon atoms), a heteroaryl group having 5to 50 ring atoms (preferably 5 to 24 ring atoms, more preferably 5 to 12ring atoms), halogen atoms such as a fluorine atom, a chlorine atom, abromine atom, and an iodine atom, and a cyano group.

It is also preferred that Ar^(c) be a group represented by the followingformula (IV).

In the formula (IV), R⁸ and R⁹ each represent a halogen atom, a linearor branched alkyl group having 1 to 50 carbon atoms, a linear orbranched alkenyl group having 1 to 50 carbon atoms, an aryl group having6 to 50 ring carbon atoms, or a heteroaryl group having 5 to 50 ringatoms.

Examples of the halogen atom, the alkyl group, the alkenyl group, thearyl group, and the heteroaryl group include the same examples as thoseof R³ and R⁴. Preferred examples thereof are also the same, and examplesof the substituent which any such group may have also include the sameexamples. The alkyl group may be substituted with a hydroxyl group.

A plurality of R⁸'s or R⁹'s adjacent to each other, or R⁸ and R⁹ may bebonded to each other to form a ring. Further, an oxygen atom or anitrogen atom may be present in the ring. A group thus formed can berepresented by, for example, the formula (II) or the formula (III)(provided that the case where X represents a sulfur atom is excludedhere), and in this case, Ar^(c) may be identical to or different fromAr^(a) and Ar^(b). When Ar^(c) represents a group different from Ar^(a)and Ar^(b), the molecular symmetry of the aromatic amine derivative canbe reduced by a group having steric hindrance. Accordingly, anintermolecular interaction is small, crystallization is suppressed, anda yield upon production of the organic EL device can be increased.

n′ represents an integer of 0 to 3. n′ preferably represents 2 or 3because of the following reason. The steric hindrance of the aromaticamine derivative is raised, and hence the intermolecular interaction isreduced and a suppressing effect on the crystallization is enhanced.

t represents an integer of 0 to 4 and u represents an integer of 0 to 5.

It should be noted that when a plurality of R⁸'s are present on the samebenzene ring or on different benzene rings, the plurality of R⁸'s may beidentical to or different from each other. In addition, when a pluralityof R⁹'s are present on the same benzene ring, the plurality of R⁹'s maybe identical to or different from each other.

The case where Ar^(c) represents a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms, especially the case where Ar^(c)is represented by an aryl group having 18 to 50 ring carbon atoms ispreferred from the following viewpoint. As steric bulkiness is raised toreduce the intermolecular interaction, the crystallization of thematerial is suppressed and the stability of a thin film is improved, andas a result, the lifetime of the organic EL device is additionallylengthened. In addition, when Ar^(c) is represented by the formula (II),Ar^(c) is preferably represented by the formula (II′) from theviewpoints of an additionally high charge mobility and an additionalreduction in the driving voltage of the organic EL device.

When Ar^(c) is represented by the formula (III), Ar^(c) may be identicalto or different from Ar^(b). In addition, when Ar^(c) is represented bythe formula (III), Ar^(c) is preferably represented by the formula(III′) from the viewpoints of an additionally high charge mobility andan additional reduction in the driving voltage of the organic EL device.

Here, specific examples of Ar^(c) are shown below. However, Ar^(c) isnot particularly limited to these examples. It should be noted that D inan exemplified compound represents a deuterium atom.

When Ar^(c) represents an aryl group, preferably a biphenyl group, aterphenyl group, a quaterphenyl group, a naphthyl group, an anthracenegroup, a fluorene group, or a phenanthrene group, more preferably aterphenyl group or a quaterphenyl group, the following effect can beexpected. As the intermolecular interaction is reduced by the raisedsteric hindrance of the aromatic amine derivative, the crystallizationis suppressed, the stability of the thin film is additionally improved,and the lifetime of the organic EL device is additionally lengthened.

In particular, in the case where Ar^(c) represents a terphenyl group ora quaterphenyl group, when benzene rings for constructing the terphenylgroup or the quaterphenyl group are bonded to one another at theirrespective para positions, such a chemical structure that a conjugatedsystem is bonded and expanded is established, and hence an increasingeffect on the charge mobility can be expected. On the other hand, whenthe benzene rings for constructing the terphenyl group or thequaterphenyl group are bonded to one another at their respective metapositions, the steric hindrance is additionally raised to reduce theintermolecular interaction, and hence the suppressing effect on thecrystallization can be additionally expected.

In addition, in the case where Ar^(c) represents a heteroaryl group,preferably a dibenzofuran group, a carbazole group, or adibenzothiophene group, more preferably a dibenzofuran group, anadditional lengthening effect on the lifetime of the organic EL devicecan be expected.

It should be noted that Ar^(c) and Ar^(a), and Ar^(c) and Ar^(b) arepreferably not of the same structure because the symmetry of thearomatic amine derivative reduces, the stability of the thin film isimproved, and the lifetime of the organic EL device is additionallylengthened. On the other hand, when Ar^(c) and Ar^(a) or Ar^(c) andAr^(b) represent groups of the same kind, their bonding positions arepreferably caused to differ from each other (in the case of, forexample, a dibenzofuranyl group, a 2-dibenzofuranyl group and a4-dibenzofuranyl group are prepared) because the symmetry of thearomatic amine derivative reduces, the stability of the thin film isimproved, and the lifetime of the organic EL device is additionallylengthened.

Next, specific examples of the aromatic amine derivative of the presentinvention represented by the formula (I) are shown below. However, thederivative is not particularly limited to these examples.

The aromatic amine derivative represented by the formula (I) of thepresent invention is useful as a material for an organicelectroluminescence device.

It should be noted that a method of producing the aromatic aminederivative of the present invention is not particularly limited, and thederivative can be produced with reference to examples of the descriptionby utilizing and applying a known method.

(Organic Electroluminescence Device)

Hereinafter, the structure of the organic EL device of the presentinvention is described.

Typical examples of the device structure of the organic EL device of thepresent invention may include, but not particularly limited to, thefollowing structures (1) to (13). It should be noted that the devicestructure (8) is preferably used.

(1) Anode/light emitting layer/cathode

(2) Anode/hole injecting layer/light emitting layer/cathode

(3) Anode/light emitting layer/electron injecting layer/cathode

(4) Anode/hole injecting layer/light emitting layer/electron injectinglayer/cathode

(5) Anode/organic semiconductor layer/light emitting layer/cathode

(6) Anode/organic semiconductor layer/electron barrier layer/lightemitting layer/cathode

(7) Anode/organic semiconductor layer/light emitting layer/adhesionimproving layer/cathode

(8) Anode/hole injecting layer/hole transporting layer/light emittinglayer/(electron transporting layer/) electron injecting layer/cathode

(9) Anode/insulating layer/light emitting layer/insulating layer/cathode

(10) Anode/inorganic semiconductor layer/insulating layer/light emittinglayer/insulating layer/cathode

(11) Anode/organic semiconductor layer/insulating layer/light emittinglayer/insulating layer/cathode

(12) Anode/insulating layer/hole injecting layer/hole transportinglayer/light emitting layer/insulating layer/cathode

(13) Anode/insulating layer/hole injecting layer/hole transportinglayer/light emitting layer/(electron transporting layer/) electroninjecting layer/cathode

In addition, in the organic EL device of the present invention, thearomatic amine derivative of the present invention, which may be used inany one of the organic thin-film layers because the derivative hardlycrystallizes, is preferably incorporated into the hole injecting layeror the hole transporting layer, more preferably incorporated into thehole transporting layer from the viewpoint of a reduction in the drivingvoltage of the organic EL device. The organic EL device using thearomatic amine derivative of the present invention not only is driven ata reduced voltage but also has high luminous efficiency and a longlifetime.

The content at which the aromatic amine derivative of the presentinvention is incorporated into one organic thin-film layer, preferablythe hole injecting layer or the hole transporting layer is preferably 30to 100 mol %, more preferably 50 to 100 mol %, still more preferably 80to 100 mol %, particularly preferably substantially 100 mol % withrespect to all components of the organic thin-film layer.

Hereinafter, each layer of the organic EL device of such a constructionthat the aromatic amine derivative of the present invention isincorporated into the hole transporting layer as a preferred embodimentis described.

(Substrate)

The organic EL device is generally prepared on a substrate havinglight-transmissive property. The substrate having light-transmissiveproperty is the substrate which supports the organic EL device. It ispreferred that the light-transmissive substrate have transmissiveproperty which is a transmittance of light of 50% or more in the visiblelight region where the wavelength is 400 to 700 nm and still preferablybe flat and smooth.

Examples of the light-transmissive substrate include a glass plate and asynthetic resin plate. In particular, examples of the glass plateinclude plates formed of soda-lime glass, glass containing barium andstrontium, lead glass, aluminosilicate glass, borosilicate glass, bariumborosilicate glass, and quartz. Further, examples of the synthetic resinplate include plates formed of a polycarbonate resin, an acrylic resin,a polyethylene terephthalate resin, a polyether sulfide resin, and apolysulfone resin.

(Anode)

The anode has a role in injecting holes to the hole transporting layeror the light emitting layer. It is effective that the anode has a workfunction of 4 eV or more (preferably 4.5 eV or more). A material for theanode used in the present invention is specifically exemplified bycarbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver,gold, platinum, palladium, and alloys thereof, metal oxides such as tinoxide and indium oxide used for an ITO substrate and an NESA substrate,and organic conductive resins such as polythiophene and polypyrrole.

The anode is obtained by forming a thin film with one of the materialsfor electrodes by, for example, a vapor deposition method or asputtering method.

As described above, when light emitted from the light emitting layer isobtained through the anode, it is preferred that the anode have atransmittance of more than 10% with respect to the emitted light. It isalso preferred that the sheet resistance of the anode be several hundredΩ/□ or less. The thickness of the anode is generally 10 nm to 1 μm,preferably 10 to 200 nm although the value varies depending onmaterials.

(Cathode)

As the cathode, a material such as a metal, an alloy, anelectroconductive compound, or a mixture of those materials, which havea small work function (4 eV or less) and are used as electrodematerials, is used. Specific examples of the electrode material to beused include, but not particularly limited to, magnesium, calcium, tin,lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum,lithium fluoride, and alloys thereof. Representative examples of thealloys include, but not particularly limited to, magnesium/silver,magnesium/indium, and lithium/aluminum. A ratio of the alloy componentsis controlled by, for example, the temperature of a vapor depositionsource, an atmosphere, and a degree of vacuum, and an appropriate ratiois selected for the ratio. The anode and the cathode may each be formedof a layer construction having two or more layers, as required.

The cathode can be obtained by forming a thin film of the electrodematerial described above in accordance with a method such as vapordeposition or sputtering.

Here, when light emitted from the light emitting layer is obtainedthrough the cathode, it is preferred that the cathode have atransmittance of more than 10% with respect to the emitted light. It isalso preferred that the sheet resistivity of the cathode be severalhundred Ω/□ or less. In addition, the thickness of the cathode isgenerally 10 nm to 1 μm, preferably 50 nm to 200 nm.

(Insulating Layer)

In addition, in general, defects in pixels are liable to be formed inorganic EL devices due to leak and short circuit because an electricfield is applied to ultra-thin films. In order to prevent the formationof the defects, an insulating layer formed of a thin-film layer havinginsulating property may be inserted between the pair of electrodes.

Examples of the material used for the insulating layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, andvanadium oxide. It should be noted that a mixture or a laminate of thosematerials may be used.

(Light Emitting Layer)

The light emitting layer of the organic EL device has a combination ofthe following functions (1) to (3).

(1) The injecting function: the function that allows holes to beinjected from the anode or the hole injecting layer and electrons to beinjected from the cathode or the electron injecting layer when anelectric field is applied.

(2) The transporting function: the function of transporting injectedcharges (i.e., electrons and holes) by the force of the electric field.

(3) The light emitting function: the function of providing the field forrecombination of electrons and holes and leading the recombination tothe emission of light.

Although the ease with which a hole is injected and the ease with whichan electron is injected may differ from each other, and transportingabilities represented by the mobilities of a hole and an electron mayvary in extent, one of the charges is preferably transferred.

A host material or a doping material which can be used in the lightemitting layer is not particularly limited, and examples thereof includecondensed ring aromatic compounds and derivatives thereof, such asnaphthalene, phananthrene, rubrene, anthracene, tetracene, pyrene,perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene,pentaphenylcyclopentadiene, fluorene, spirofluorene,9,10-diphenylanthracene, 9,10-bis(phenylethynyl)anthracene, and1,4-bis(9′-ethynylanthracenyl)benzene, organic metal complexes such astris(8-quinolinolato)aluminum andbis-(2-methyl-8-quinolinolato)-4-(phenylphenolinato)aluminum, anarylamine derivative, a styrylamine derivative, a stilbene derivative, acoumarin derivative, a pyrane derivative, an oxazone derivative, abenzothiazole derivative, a benzoxazole derivative, a benzimidazolederivative, a pyrazine derivative, a cinnamate derivative, adiketopyrrolopyrrole derivative, an acridone derivative, andquinacridone derivative. Of those, an arylamine derivative, astyrylamine derivative are preferred, and a styrylamine derivative ismore preferred.

An additional known light emitting material, doping material, holeinjecting material, or electron injecting material as well as thearomatic amine derivative of the present invention can be used in theplurality of layers as required. Alternatively, the aromatic aminederivative of the present invention can be used as a doping material.

Reductions in the luminance and lifetime of the organic EL device due toquenching can be prevented by providing the organic thin-film layerswith a multilayer structure. A light emitting material, a dopingmaterial, a hole injecting material, and an electron injecting materialcan be used in combination as required. In addition, the doping materialenables the achievement of improvements in emission luminance andluminous efficiency, and of the emission of red or blue light.

In addition, each of the hole injecting layer, the light emitting layer,and the electron injecting layer may be formed of a layer constructionhaving two or more layers. At that time, in the case of the holeinjecting layer, a layer into which a hole is injected from an electrodeis referred to as “hole injecting layer,” and a layer that receives thehole from the hole injecting layer and transports the hole to the lightemitting layer is referred to as “hole transporting layer.” Similarly,in the case of the electron injecting layer, a layer into which anelectron is injected from an electrode is referred to as “electroninjecting layer,” and a layer that receives the electron from theelectron injecting layer and transports the electron to the lightemitting layer is referred to as “electron transporting layer.”

Each of those layers is selected and used in consideration of variousfactors such as the energy level of a material therefor, its heatresistance, and its adhesiveness with an organic layer or a metalelectrode.

(Hole Injecting Layer and Hole Transporting Layer)

The hole injecting layer and the hole transporting layer are layerswhich help injection of holes into the light emitting layer andtransports the holes to the light emitting region. The layers eachexhibit a great mobility of holes and, in general, have an ionizationenergy as small as 5.7 eV or less. As such hole injecting layer and holetransporting layer, a material which transports holes to the lightemitting layer under an electric field of a smaller strength ispreferred. A material which exhibits, for example, a mobility of holesof 10⁻⁴ cm²/V·sec or more under application of an electric field of 10⁴to 10⁶ V/cm is preferred.

As described above, the aromatic amine derivative of the presentinvention is particularly preferably used in the hole transportinglayer.

When the aromatic amine derivative of the present invention is used inthe hole transporting layer, the aromatic amine derivative of thepresent invention may be used alone or as a mixture with any othermaterial for forming the hole transporting layer.

The other material which can be used as a mixture with the aromaticamine derivative of the present invention for forming the holetransporting layer is not particularly limited as long as the materialhas the preferred property. The material can be arbitrarily selectedfrom materials which are conventionally used as hole transportingmaterials in photoconductive materials and known materials which areused for hole transporting layers in organic EL devices. In thedescription, a material that has a hole transporting ability and can beused in a hole transporting zone is referred to as “hole transportingmaterial.”

Specific examples of the other material for a hole transporting layerthan the aromatic amine derivative of the present invention include, butnot particularly limited to, a phthalocyanine derivative, anaphthalocyanine derivative, a porphyrin derivative, oxazole,oxadiazole, triazole, imidazole, imidazolone, imidazolethione,pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole,hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidinetype triphenylamine, styrylamine type triphenylamine, diamine typetriphenylamine, derivatives thereof, and polymer materials such aspolyvinyl carbazole, polysilane, and a conductive polymer.

Of the hole injecting materials that can be used in the organic ELdevice of the present invention, more effective hole injecting materialsare an aromatic tertiary amine derivative and a phthalocyaninederivative.

Examples of the aromatic tertiary amine derivative include, but notparticularly limited to, triphenylamine, tritolylamine,tolyldiphenylamine,N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1′-biphenylyl-4,4′-diamine,N,N,N′,N′-(4-methylphenyl)-1,1′-phenyl-4,4′-diamine,N,N,N′,N′-(4-methylphenyl)-1,1′-biphenylyl-4,4′-diamine,N,N′-diphenyl-N,N′-dinaphthyl-1,1′-biphenylyl-4,4′-diamine,N,N′-(methylphenyl)-N,N′-(4-n-butylphenyl)-phenanthrene-9,10-diamine,N,N-bis(4-di-4-tolylaminophenyl)-4-phenyl-cyclohexane, and an oligomeror a polymer having one of the aromatic tertiary amine skeletons.

Examples of the phthalocyanine (Pc) derivative include, but not limitedto, phthalocyanine derivatives such as H₂Pc, CuPc, CoPc, NiPc, ZnPc,PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl₂SiPc, (HO)AlPc,(HO)GaPc, VOPc, TiOPc, MoOPc, and GaPc-O—GaPc, and naphthalocyaninederivatives. In addition, the organic EL device of the present inventionpreferably has formed therein a layer containing any such aromatictertiary amine derivative and/or any such phthalocyanine derivative, forexample, the hole transporting layer or the hole injecting layer betweena light emitting layer and an anode.

A material for the hole injecting layer is not particularly limited aslong as the material has the preferred properties. An arbitrary materialselected from a material conventionally used as a hole injectingmaterial in a photoconductive material and a known material used in thehole transporting layer of an organic EL device can be used. In thedescription, a material that has a hole injecting ability and can beused in a hole injection zone is referred to as “hole injectingmaterial.”

In particular, in the organic EL device of the present invention, ahexaazatriphenylene compound represented by the following formula (A) ispreferably used as a hole injecting material.

In the formula (A), R¹¹¹ to R¹¹⁶ each independently represent a cyanogroup, —CONH₂, a carboxyl group, or —COOR¹¹⁷ (where R¹¹⁷ represents analkyl group having 1 to 20 carbon atoms), or R¹¹¹ and R¹¹², R¹¹³ andR¹¹⁴, or R¹¹⁵ and R¹⁶ combine with each other to represent a grouprepresented by —CO—O—CO—.

It should be noted that when R¹¹¹ to R¹¹⁶ each represent a cyano group,—CONH₂, a carboxyl group, or —COOR¹¹⁷, R¹¹¹ to R¹¹⁶ preferably representthe same group. When R¹¹¹ and R¹¹², R¹¹³ and R¹¹⁴, or R¹¹⁵ and R¹¹⁶combine with each other to represent a group represented by —CO—O—CO—,each of the pairs preferably represents a group represented by—CO—O—CO—.

(Electron Injecting Layer and Electron Transporting Layer)

Each of the electron injecting layer and the electron transporting layeris a layer which helps injection of electrons into the light emittinglayer, transports the electrons to the light emitting region, andexhibits a great mobility of electrons. Further, the adhesion improvinglayer is an electron injecting layer including a material exhibitingparticularly improved adhesion with the cathode.

In addition, it is known that, in an organic EL device, emitted light isreflected by an electrode (cathode in this case), and hence emittedlight directly extracted from an anode and emitted light extracted viathe reflection by the electrode interfere with each other. The thicknessof an electron transporting layer is appropriately selected from therange of several nanometers to several micrometers in order that theinterference effect may be effectively utilized. In particular, when thethickness of the electron transporting layer is large, an electronmobility is preferably at least 10⁻⁵ cm²/V·s or more upon application ofan electric field of 10⁴ to 10⁶ V/cm in order to avoid an increase involtage.

Specific examples of the material to be used for the electron injectinglayer include fluorenone, anthraquinodimethane, diphenoquinone,thiopyranedioxide, oxazole, oxadiazole, triazole, imidazole,perylenetetracarboxylic acid, fluorenylidenemethane,anthraquinodimethane, anthrone, and derivatives thereof, but thematerial is not particularly limited thereto. In addition, anelectron-accepting substance can be added to the hole injecting materialor an electron-donating substance can be added to the electron injectingmaterial to thereby sensitize the hole injecting material or theelectron injecting material, respectively.

In the organic EL device of the present invention, more effectiveelectron injecting materials are a metal complex compound and anitrogen-containing five-membered ring derivative.

Examples of the metal complex compound include, but not particularlylimited to, 8-hydroxyquinolinatolithium,tris(8-hydroxyquinolinato)aluminum, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum.

Examples of the nitrogen-containing five-membered ring derivativepreferably include, an oxazole derivative, a thiazole derivative, anoxadiazole derivative, a thiadiazole derivative, and a triazolederivative.

In the organic EL device of the present invention, thenitrogen-containing five-membered ring derivative is particularlypreferably a benzimidazole derivative represented by any one of thefollowing formulae (1) to (3).

In the formulae (1) to (3), Z¹, Z², and Z³ each independently representa nitrogen atom or a carbon atom.

R¹¹ and R¹² each independently represent a substituted or unsubstitutedaryl group having 6 to 60 carbon atoms, a substituted or unsubstitutedheteroaryl group having 3 to 60 carbon atoms, an alkyl group having 1 to20 carbon atoms, an alkyl group having 1 to 20 carbon atoms andsubstituted with a halogen atom, or an alkoxy group having 1 to 20carbon atoms.

m represents an integer of 0 to 5, and when m represents an integer of 2or more, a plurality of R¹¹'s may be identical to or different from eachother. In addition, a plurality of R¹¹'s adjacent to each other may bebonded to each other to form a substituted or unsubstituted aromatichydrocarbon ring. Examples of the substituted or unsubstituted aromatichydrocarbon ring which the plurality of R¹¹'s adjacent to each other arebonded to each other to represent when m represents an integer of 2 ormore include a benzene ring, a naphthalene ring, and an anthracene ring.

Ar¹ represents a substituted or unsubstituted aryl group having 6 to 60carbon atoms, or a substituted or unsubstituted heteroaryl group having3 to 60 carbon atoms.

Ar² represents a hydrogen atom, an alkyl group having 1 to carbon atoms,an alkyl group having 1 to 20 carbon atoms and substituted with ahalogen atom, an alkoxy group having 1 to 20 carbon atoms, a substitutedor unsubstituted aryl group having 6 to 60 carbon atoms, or asubstituted or unsubstituted heteroaryl group having 3 to 60 carbonatoms.

Ar³ represents a substituted or unsubstituted arylene group having 6 to60 carbon atoms, or a substituted or unsubstituted heteroarylene grouphaving 3 to 60 carbon atoms.

L¹, L², and L³ each independently represent a single bond, a substitutedor unsubstituted arylene group having 6 to 60 carbon atoms, asubstituted or unsubstituted heterofused ring group having 9 to 60 ringatoms, or a substituted or unsubstituted fluorenylene group.

In the organic EL device of the present invention, a light emittingmaterial, a doping material, a hole injecting material, or an electroninjecting material may be incorporated into the layer containing thearomatic amine derivative of the present invention.

In addition, the surface of the organic EL device obtained by thepresent invention can be provided with a protective layer, or theentirety of the device can be protected with silicone oil, a resin, orthe like from the viewpoint of an improvement in the stability of thedevice against a temperature, a humidity, an atmosphere, or the like.

Any one of dry film forming methods such as vacuum deposition,sputtering, plasma, and ion plating, and wet film forming methods suchas spin coating, dipping, and flow coating is applicable to theformation of each layer of the organic EL device of the presentinvention.

The thickness of each layer is not particularly limited, but may be setto an appropriate thickness as an organic EL device. An excessivelylarge thickness requires an increased applied voltage for obtainingcertain optical output, resulting in poor efficiency. An excessivelysmall thickness causes a pin hole or the like, with the result thatsufficient emission luminance cannot be obtained even when an electricfield is applied. In general, the thickness is in the range ofpreferably 5 nm to 10 μm, or more preferably nm to 0.2 μm.

In the case of a wet film forming method, a material of which each layeris formed is dissolved or dispersed into an appropriate solvent such asethanol, chloroform, tetrahydrofuran, or dioxane, to thereby form a thinfilm. At that time, any one of the above solvents may be used.

An organic EL material-containing solution containing the aromatic aminederivative of the present invention as an organic EL material and asolvent can be used as a solution suitable for such wet film formingmethod. In addition, an appropriate resin or additive may be used ineach of the organic thin-film layers for, for example, improving filmformability or preventing a pin hole in the layer. Examples of the resininclude: insulating resins such as polystyrene, polycarbonate,polyallylate, polyester, polyamide, polyurethane, polysulfone,polymethyl methacrylate, polymethyl acrylate, and cellulose, andcopolymers thereof; photoconductive resins such as poly-N-vinylcarbazoleand polysilane; and conductive resins such as polythiophene andpolypyrrole. Examples of the additive include an antioxidant, a UVabsorber, and a plasticizer.

EXAMPLES

Hereinafter, the present invention is specifically described by way ofexamples. However, the present invention is by no means limited by theseexamples.

It should be noted that the structures of intermediates synthesized inSynthesis Examples 1 to 23 below are as shown below.

Synthesis Example 1 Synthesis of Intermediate-1

In a stream of argon, 47 g of 4-bromobiphenyl, 23 g of iodine, 9.4 g ofperiodic acid dihydrate, 42 ml of water, 360 ml of acetic acid, and 11ml of sulfuric acid were loaded into a 1,000-ml three-necked flask, andthe mixture was stirred at 65° C. for 30 minutes and was then subjectedto a reaction at 90° C. for 6 hours. The reactant was poured into icewater, followed by filtering. The resultant was washed with water, andthen washed with methanol, whereby 67 g of a white powder were obtained.

Main peaks having ratios m/z of 358 and 360 were obtained with respectto C₁₂H₈BrI=359 by a field desorption mass spectrometry (hereinafter,referred to as FD-MS) analysis, so the powder was identified as theintermediate-1.

Synthesis Example 2 Synthesis of Intermediate-2

Under an argon atmosphere, 12.5 g of 2-bromofluorene, 0.7 g ofbenzyltriethylammonium chloride, 60 ml of dimethyl sulfoxide, 8.0 g ofsodium hydroxide, and 17 g of methyl iodide were loaded into a 200-mlthree-necked flask, and then the mixture was subjected to a reaction for18 hours.

After the completion of the reaction, water and ethyl acetate were addedto perform separation and extraction. After that, the resultant wasconcentrated, and then the resultant coarse product was purified bysilica gel chromatography (hexane). Thus, 12.4 g of a yellow oilysubstance were obtained. The substance was identified as theintermediate-2 by FD-MS analysis.

Synthesis Example 3 Synthesis of Intermediate-3

A reaction was performed in the same manner as in Synthesis Example 1except that 2-bromo-9,9-dimethylfluorene was used instead of4-bromobiphenyl. As a result, 61 g of a white powder were obtained. Thepowder was identified as the intermediate-3 by FD-MS analysis.

Synthesis Example 4 Synthesis of Intermediate-4

Under an argon atmosphere, 39.9 g of the intermediate-3, 12.8 g ofphenylboronic acid, 2.31 g of tetrakis(triphenylphosphine)palladium, 300ml of toluene, and 150 ml of an aqueous solution of sodium carbonatehaving a concentration of 2 M were loaded into a 1,000-ml three-neckedflask, and then the mixture was heated for 10 hours while beingrefluxed.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 27.3 g of a whitecrystal were obtained. The crystal was identified as the intermediate-4by FD-MS analysis.

Synthesis Example 5 Synthesis of Intermediate-5

17.7 Grams of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g ofpotassium iodate, 5.9 ml of sulfuric acid, and ethanol were loaded intoa 200-ml three-necked flask, and then the mixture was subjected to areaction at 75° C. for 2 hours.

After the resultant had been cooled, water and ethyl acetate were addedto perform separation and extraction. After that, the organic layer waswashed with baking soda water and water, and was then concentrated. Theresultant coarse product was purified by silica gel chromatography(toluene), and then the resultant solid was dried under reducedpressure. Thus, 21.8 g of a white solid were obtained. The solid wasidentified as the intermediate-5 by FD-MS analysis.

Synthesis Example 6 Synthesis of Intermediate-6

In a stream of argon, 13.1 g of the intermediate-5, dehydrated toluene,and dehydrated ether were loaded into a 300-ml three-necked flask, andthen the mixture was cooled to −45° C. 25 Milliliters of a solution(1.58 M) of n-butyllithium in hexane were dropped to the mixture, andthen the temperature was increased to −5° C. over 1 hour while themixture was stirred. The mixture was cooled to −45° C. again, and then25 ml of boronic acid triisopropyl ester were slowly dropped to themixture. After that, the mixture was subjected to a reaction for 2hours.

After the temperature of the resultant had been returned to roomtemperature, a 10% diluted hydrochloric acid solution was added to theresultant, and then the mixture was stirred so that an organic layer wasextracted. After having been washed with a saturated salt solution, theorganic layer was dried with anhydrous magnesium sulfate and separatedby filtration. After that, the separated product was concentrated. Theresultant solid was purified by silica gel chromatography (toluene), andthen the resultant solid was washed with n-hexane and dried underreduced pressure. Thus, 7.10 g of a solid were obtained. The solid wasidentified as the intermediate-6 by FD-MS analysis.

Synthesis Example 7 Synthesis of Intermediate-7

Under an argon atmosphere, 35.9 g of the intermediate-1, 30.1 g of theintermediate-6, 2.31 g of tetrakis(triphenylphosphine)palladium, 300 mlof toluene, and 150 ml of an aqueous solution of sodium carbonate havinga concentration of 2 M were loaded into a 1,000-ml three-necked flask,and then the mixture was heated for 10 hours while being refluxed.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 24.2 g of a whitecrystal were obtained. The crystal was identified as the intermediate-7by FD-MS analysis.

Synthesis Example 8 Synthesis of Intermediate-8

A reaction was performed in the same manner as in Synthesis Example 6except that 16.8 g of the intermediate-7 were used instead of theintermediate-5. Thus, 10.1 g of a white powder were obtained. The powderwas identified as the intermediate-8 by FD-MS analysis.

Synthesis Example 9 Synthesis of Intermediate-9

A reaction was performed in the same manner as in Synthesis Example 7except that: 28.3 g of 4-iodobromobenzene were used instead of theintermediate-1; and 46.1 g of the intermediate-8 were used instead ofthe intermediate-6. Thus, 33 g of a white powder were obtained. Thepowder was identified as the intermediate-9 by FD-MS analysis.

Synthesis Example 10 Synthesis of Intermediate-10

Under a nitrogen atmosphere, 150 g of dibenzofuran and 1 l of aceticacid were loaded into a 300-ml three-necked flask, and then the contentswere dissolved under heat. 188 Grams of bromine were added dropwise tothe solution. After that, the mixture was stirred for 20 hours under aircooling. The precipitated crystal was separated by filtration, and wasthen sequentially washed with acetic acid and water. The washed crystalwas dried under reduced pressure. The resultant crystal was purified bydistillation under reduced pressure, and was then repeatedlyrecrystallized with methanol several times. Thus, 66.8 g of2-bromodibenzofuran were obtained.

Under an argon atmosphere, 24.7 g of 2-bromodibenzofuran and 400 ml ofanhydrous THF were loaded into a 1,000-ml three-necked flask, and then63 ml of a solution of n-butyllithium in hexane having a concentrationof 1.6 M were added to the mixture during the stirring of the mixture at−40° C. The reaction solution was stirred for 1 hour while being heatedto 0° C. The reaction solution was cooled to −78° C. again, and then asolution of 26.0 g of trimethyl borate in 50 ml of dry THF was droppedto the solution. The reaction solution was stirred at room temperaturefor 5 hours.

200 Milliliters of 1N hydrochloric acid were added to the solution, andthen the mixture was stirred for 1 hour. After that, the aqueous layerwas removed. The organic layer was dried with magnesium sulfate, andthen the solvent was removed by distillation under reduced pressure. Theresultant solid was washed with toluene. Thus, 15.2 g ofdibenzofuran-2-boronic acid were obtained.

Synthesis Example 11 Synthesis of Intermediate-1

A reaction was performed in the same manner as in Synthesis Example 7except that 22.3 g of the intermediate-10 were used instead of theintermediate-6. Thus, 28.7 g of a white powder were obtained. The powderwas identified as the intermediate-11 by FD-MS analysis.

Synthesis Example 12 Synthesis of Intermediate-12

A reaction was performed in the same manner as in Synthesis Example 7except that 22.3 g of dibenzofuran-4-boronic acid were used instead ofthe intermediate-6. Thus, 31.9 g of a white powder were obtained. Thepowder was identified as the intermediate-12 by FD-MS analysis.

Synthesis Example 13 Synthesis of Intermediate-13

Under an argon atmosphere, 7.0 g of acetamide, 45.8 g of theintermediate-2, 6.8 g of copper(I) iodide, 6.3 g ofN,N′-dimethylethylenediamine, 51 g of tripotassium phosphate, and 300 mlof xylene were loaded into a 500-ml three-necked flask, and then themixture was subjected to a reaction at 140° C. for 36 hours. Afterhaving been cooled, the resultant was filtrated and washed with toluene.The washed product was further washed with water and methanol, and wasthen dried. Thus, 19 g of a pale yellow powder were obtained. The powderwas identified as the intermediate-13 by FD-MS analysis.

Synthesis Example 14 Synthesis of Intermediate-14

31.0 Grams of the intermediate-13, 26 g of potassium hydroxide, 28 ml ofion-exchanged water, 39 ml of xylene, and 77 ml of ethanol were loadedinto a 300-ml three-necked flask, and then the mixture was heated for 36hours while being refluxed. After the completion of the reaction, theresultant was extracted with toluene and dried with magnesium sulfate.The dried product was concentrated under reduced pressure, and then theresultant coarse product was subjected to column purification. Thepurified product was recrystallized with toluene, and then therecrystallized product was taken by filtration. After that, theresultant was dried. Thus, 15.8 g of a white powder were obtained. Thepowder was identified as the intermediate-14 by FD-MS analysis.

Synthesis Example 15 Synthesis of Intermediate-15

A reaction was performed in the same manner as in Synthesis Examples 13and 14 except that 15 g of the intermediate-13 were used instead ofacetamide and 19.6 g of 4-bromobiphenyl were used instead of theintermediate-2 upon performance of Synthesis Examples 13 and 14 in thestated order. Thus, 13 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-15 by FD-MS analysis.

Synthesis Example 16 Synthesis of Intermediate-16

A reaction was performed in the same manner as in Synthesis Examples 13and 14 except that 8.1 g of acetanilide were used instead of acetamideand 29.3 g of the intermediate-4 were used instead of the intermediate-2upon performance of Synthesis Examples 13 and 14 in the stated order.Thus, 14 g of a pale yellow powder were obtained. The powder wasidentified as the intermediate-16 by FD-MS analysis.

Synthesis Example 17 Synthesis of Intermediate-17

A reaction was performed in the same manner as in Synthesis Examples 13and 14 except that 15 g of the intermediate-13 were used instead of theacetamide upon performance of Synthesis Examples 13 and 14 in the statedorder. Thus, 14.4 g of a pale yellow powder were obtained. The powderwas identified as the intermediate-17 by FD-MS analysis.

Synthesis Example 18 Synthesis of Intermediate-18

A reaction was performed in the same manner as in Synthesis Examples 13and 14 except that 15 g of the intermediate-13 were used instead ofacetamide and 26 g of 4-bromo-p-terphenyl were used instead of theintermediate-2 upon performance of Synthesis Examples 13 and 14 in thestated order. Thus, 15.5 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-18 by FD-MS analysis.

Synthesis Example 19 Synthesis of Intermediate-19

A reaction was performed in the same manner as in Synthesis Examples 13and 14 except that 32 g of the intermediate-4 were used instead of theintermediate-2 upon performance of Synthesis Examples 13 and 14 in thestated order. Thus, 11 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-19 by FD-MS analysis.

Synthesis Example 20 Synthesis of Intermediate-20

A reaction was performed in the same manner as in Synthesis Example 6except that 33 g of the intermediate-2 were used instead of theintermediate-5. Thus, 17 g of a white powder were obtained. The powderwas identified as the intermediate-20 by FD-MS analysis.

Synthesis Example 21 Synthesis of Intermediate-21

A reaction was performed in the same manner as in Synthesis Example 9except that 17 g of the intermediate-20 were used instead of theintermediate-8. Thus, 20 g of a white powder were obtained. The powderwas identified as the intermediate-21 by ED-MS analysis.

Synthesis Example 22 Synthesis of Intermediate-22

A reaction was performed in the same manner as in Synthesis Example 13except that 20 g of the intermediate-21 were used instead of theintermediate-2. Thus, 12 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-22 by FD-MS analysis.

Synthesis Example 23 Synthesis of Intermediate-23

A reaction was performed in the same manner as in Synthesis Examples 13and 14 except that 12 g of the intermediate-22 were used instead ofacetamide and 12.8 g of 4-bromobiphenyl were used instead of theintermediate-2 upon performance of Synthesis Examples 13 and 14 in thestated order. Thus, 10.4 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-23 by FD-MS analysis.

Shown below are the structures of the aromatic amine derivatives of thepresent invention produced in Examples-of-Synthesis 1 to 18 below.

In addition, a method of measuring the hole mobility of each of thearomatic amine derivatives (H-1) to (H-18) of the present inventionproduced in the examples-of-synthesis below is described below.

(Measurement of Hole Mobility)

The hole mobility was measured by a time-of-flight method (TOF) Each ofthe aromatic amine derivatives (H-1) to (H-18) produced inExamples-of-Synthesis 1 to 18 below was formed into a film having athickness of 2.5 to 3.0 μm on an ITO substrate, and Al was furtherprovided as a counter electrode.

A voltage was applied between both the electrodes at an electric fieldintensity of 0.1 to 0.6 MV/cm, N₂ laser light (pulse width: 2 ns) wasapplied, and a generated current was measured with a storageoscilloscope (measuring frequency band: 300 MHz). The hole mobility wasdetermined in accordance with an ordinary analysis method from a time τat which the shoulder of a photocurrent appeared (time at which thephotocurrent attenuated) with an equation “μ=d/(τ·E) (i: the holemobility, E: the electric field intensity, d: the thickness).”

Example-of-Synthesis 1 Production of aromatic amine Derivative (H-1)

In a stream of argon, 9.5 g of the intermediate-7, 7.2 g of theintermediate-15, 2.6 g of t-butoxysodium, 92 mg oftris(dibenzylideneacetone)dipalladium, 42 mg of tri-t-butylphosphine,and 100 ml of dehydrated toluene were loaded into a 300-ml three-neckedflask, and then the mixture was subjected to a reaction at 80° C. for 8hours.

After having been cooled, the reaction product was poured into 500 ml ofwater, and then the mixture was subjected to celite filtration. Thefiltrate was extracted with toluene and dried with anhydrous magnesiumsulfate. The dried product was concentrated under reduced pressure, andthen the resultant coarse product was subjected to column purification.The purified product was recrystallized with toluene, and then therecrystallized product was taken by filtration. After that, theresultant was dried. Thus, 8.1 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-1) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-1) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 2 Production of Aromatic Amine Derivative (H-2)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 7.2 g of the intermediate-16 were used instead of theintermediate-15. Thus, 7.8 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-2) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-2) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 3 Production of Aromatic Amine Derivative (H-3)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 8.0 g of the intermediate-17 were used instead of theintermediate-15. Thus, 8.0 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-3) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-3) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 4 Production of Aromatic Amine Derivative (H-4)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 8.8 g of the intermediate-18 were used instead of theintermediate-15. Thus, 6.8 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-4) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-4) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 5 Production of Aromatic Amine Derivative (H-5)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 11.1 g of the intermediate-19 were used instead of theintermediate-15. Thus, 8.5 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-5) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-5) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 6 Production of Aromatic Amine Derivative (H-6)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 11.0 g of the intermediate-9 were used instead of theintermediate-7. Thus, 8.3 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-6) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-6) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 7 Production of Aromatic Amine Derivative (H-7)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 8.0 g of the intermediate-11 were used instead of theintermediate-7. Thus, 7.2 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-7) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-7) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 8 Production of Aromatic Amine Derivative (H-8)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 8.0 g of the intermediate-11 were used instead of theintermediate-7; and 7.2 g of the intermediate-16 were used instead ofthe intermediate-15. Thus, 7.2 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-8) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-8) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 9 Production of Aromatic Amine Derivative (H-9)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 8.0 g of the intermediate-11 were used instead of theintermediate-7; and 8.0 g of the intermediate-17 were used instead ofthe intermediate-15. Thus, 7.5 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-9) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-9) was measured bythe method. Table 1 shows the result.

Example-of-Synthesis 10 Production of Aromatic Amine Derivative (H-10)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 8.0 g of the intermediate-11 were used instead of theintermediate-7; and 8.8 g of the intermediate-18 were used instead ofthe intermediate-15. Thus, 6.3 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-10) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-10) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 11 Production of Aromatic Amine Derivative (H-11)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 8.0 g of the intermediate-12 were used instead of theintermediate-7. Thus, 7.1 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-11) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-11) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 12 Production of Aromatic Amine Derivative (H-12)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 8.0 g of the intermediate-12 were used instead of theintermediate-7; and 7.2 g of the intermediate-16 were used instead ofthe intermediate-15. Thus, 7.1 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-12) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-12) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 13 Production of Aromatic Amine Derivative (H-13)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 8.0 g of the intermediate-12 were used instead of theintermediate-7; and 8.0 g of the intermediate-17 were used instead ofthe intermediate-15. Thus, 7.3 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-13) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-13) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 14 Production of Aromatic Amine Derivative (H-14)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 8.0 g of the intermediate-12 were used instead of theintermediate-7; and 8.8 g of the intermediate-18 were used instead ofthe intermediate-15. Thus, 6.1 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-14) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-14) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 15 Production of Aromatic Amine Derivative (H-15)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 2.1 g of the intermediate-14 were used instead of theintermediate-15. Thus, 6.1 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-15) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-15) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 16 Production of Aromatic Amine Derivative (H-16)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 2.1 g of the intermediate-14 were used instead of theintermediate-15; and 8.0 g of the intermediate-11 were used instead ofthe intermediate-7. Thus, 7.0 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-16) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-16) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 17 Production of Aromatic Amine Derivative (H-17)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that: 2.1 g of the intermediate-14 were used instead of theintermediate-15; and 8.0 g of the intermediate-12 were used instead ofthe intermediate-7. Thus, 7.2 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-17) byFD-MS analysis.

The hole mobility of the aromatic amine derivative (H-17) was measuredby the method. Table 1 shows the result.

Example-of-Synthesis 18 Production of Aromatic Amine Derivative (H-18)

A reaction was performed in the same manner as in Example-of-Synthesis 1except that 8.8 g of the intermediate-23 were used instead of theintermediate-15. Thus, 7.5 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-18) by FD-MSanalysis.

The hole mobility of the aromatic amine derivative (H-18) was measuredby the method. Table 1 shows the result.

TABLE 1 Example-of- Hole transporting Hole mobility Synthesis material(×10⁻⁴ cm²/V · s) 1 H-1  6.5 2 H-2  5.5 3 H-3  5.6 4 H-4  5.5 5 H-5  5.66 H-6  6.4 7 H-7  7.6 8 H-8  6.5 9 H-9  7.2 10 H-10 6.6 11 H-11 7.5 12H-12 6.7 13 H-13 7.0 14 H-14 6.2 15 H-15 6.7 16 H-16 7.5 17 H-17 7.2 18H-18 5.1

It was shown that the group of compounds of the present invention hadsufficient hole mobilities in the measurement by the time-of-flightmethod (TOF) and were useful as hole transporting materials.

In addition, an organic EL device using, as a hole transportingmaterial, an aromatic amine derivative produced by using any one of thefollowing intermediates was produced, and the current efficiency andluminescent color of the organic EL device, and the half lifetime of itslight emission when the device was driven with a DC constant current atan initial luminance of 5,000 cd/m² and room temperature were measured.

Synthesis Example 24 Synthesis of Intermediate-1′

Under an argon atmosphere, 47 g of 4-bromobiphenyl, 23 g of iodine, 9.4g of periodic acid dihydrate, 42 ml of water, 360 ml of acetic acid, and11 ml of sulfuric acid were loaded into a 1,000-ml three-necked flask,and the mixture was stirred at 65° C. for 30 minutes and was thensubjected to a reaction at 90° C. for 6 hours. The reaction product waspoured into ice water, followed by filtering. The resultant was washedwith water, and then washed with methanol, whereby 67 g of a whitepowder were obtained.

Main peaks having ratios m/z of 358 and 360 were obtained with respectto C₁₂H₈BrI=359 by a field desorption mass spectrometry (hereinafter,referred to as FD-MS) analysis, so the powder was identified as theintermediate-1′.

Synthesis Example 25 Synthesis of Intermediate-2′

Under an argon atmosphere, 12.5 g of 2-bromofluorene, 0.7 g ofbenzyltriethylammonium chloride, 60 ml of dimethyl sulfoxide, 8.0 g ofsodium hydroxide, and 17 g of methyl iodide were loaded into a 200-mlthree-necked flask, and then the mixture was subjected to a reaction for18 hours.

After the completion of the reaction, water and ethyl acetate were addedto perform separation and extraction. After that, the resultant wasconcentrated, and then the resultant coarse product was purified bysilica gel chromatography (hexane). Thus, 12.4 g of a yellow oilysubstance were obtained. The substance was identified as theintermediate-2′ by FD-MS analysis.

Synthesis Example 26 Synthesis of Intermediate-3′

A reaction was performed in the same manner as in Synthesis Example 24except that 55 g of the intermediate-2′ was used instead of4-bromobiphenyl. As a result, 61 g of a white powder were obtained. Thepowder was identified as the intermediate-3′ by FD-MS analysis.

Synthesis Example 27 Synthesis of Intermediate-4′

Under an argon atmosphere, 39.9 g of the intermediate-3′, 12.8 g ofphenylboronic acid, 2.31 g of tetrakis(triphenylphosphine)palladium, 300ml of toluene, and 150 ml of an aqueous solution of sodium carbonatehaving a concentration of 2 M were loaded into a 1,000-ml three-neckedflask, and then the mixture was heated for 10 hours while beingrefluxed.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 27.3 g of a whitecrystal were obtained. The crystal was identified as the intermediate-4′by FD-MS analysis.

Synthesis Example 28 Synthesis of Intermediate-5′

250 Grams of m-terphenyl, 50 g of hydroiodic acid dihydrate, 75 g ofiodine, 750 ml of acetic acid, and 25 ml of concentrated sulfuric acidwere loaded into a 2,000-ml three-necked flask, and then the mixture wassubjected to a reaction at 70° C. for 3 hours. After the reaction, theresultant was poured into 5 l of methanol, and then the mixture wasstirred for 1 hour. The resultant crystal, which had been taken from themixture by filtration, was purified by means of column chromatography,and was then recrystallized with acetonitrile. Thus, 64 g of a whitepowder were obtained. The powder was identified as the intermediate-5′by FD-MS analysis.

Synthesis Example 29 Synthesis of Intermediate-6′

17.7 Grams of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g ofpotassium iodate, 5.9 ml of sulfuric acid, and ethanol were loaded intoa 200-ml three-necked flask, and then the mixture was subjected to areaction at 75° C. for 2 hours.

After the resultant had been cooled, water and ethyl acetate were addedto perform separation and extraction. After that, the organic layer waswashed with baking soda water and water, and was then concentrated. Theresultant coarse product was purified by silica gel chromatography(toluene), and then the resultant solid was dried under reducedpressure. Thus, 21.8 g of a white solid were obtained. The solid wasidentified as the intermediate-6′ by FD-MS analysis.

Synthesis Example 30 Synthesis of Intermediate-7′

Under an argon atmosphere, 13.1 g of the intermediate-6′, dehydratedtoluene, and dehydrated ether were loaded into a 300-ml three-neckedflask, and then the mixture was cooled to −45° C. 25 Milliliters of asolution (1.58 M) of n-butyllithium in hexane were dropped to themixture, and then the temperature was increased to −5° C. over 1 hourwhile the mixture was stirred. The mixture was cooled to −45° C. again,and then 25 ml of boronic acid triisopropyl ester were slowly dropped tothe mixture. After that, the mixture was subjected to a reaction for 2hours.

After the temperature of the resultant had been returned to roomtemperature, a 10% diluted hydrochloric acid solution was added to theresultant, and then the mixture was stirred so that an organic layer wasextracted. After having been washed with a saturated salt solution, theorganic layer was dried with anhydrous magnesium sulfate and separatedby filtration. After that, the separated product was concentrated. Theresultant solid was purified by silica gel chromatography (toluene), andthen the resultant solid was washed with n-hexane and dried underreduced pressure. Thus, 7.10 g of a solid were obtained. The solid wasidentified as the intermediate-7′ by FD-MS analysis.

Synthesis Example 31 Synthesis of Intermediate-8′

Under an argon atmosphere, 28.3 g of 4-iodobromobenzene, 30.1 g ofIntermediate-7′, 2.31 g of tetrakis(triphenylphosphine)palladium, 300 mlof toluene, and 150 ml of an aqueous solution of sodium carbonate havinga concentration of 2 M were loaded into a 1,000-ml three-necked flask,and then the mixture was heated for 10 hours while being refluxed.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 20.2 g of a whitecrystal were obtained. The crystal was identified as the intermediate-8′by FD-MS analysis.

Synthesis Example 32 Synthesis of Intermediate-9′

Under an argon atmosphere, 36 g of Intermediate-1′, 16.7 g of carbazole,0.2 g of copper iodide (CuI), 42.4 g of tripotassium phosphate, 2 ml oftrans-1,2-cyclohexanediamine, and 300 ml of 1,4-dioxane were loaded intoa 1,000-ml three-necked flask, and then the mixture was stirred at 100°C. for 20 hours.

After the completion of the reaction, 300 ml of water were added to theresultant. After that, the mixture was subjected to liquid separation,and then the aqueous layer was removed. The organic layer was dried withsodium sulfate, and was then concentrated. The residue was purified bysilica gel column chromatography. Thus, 23.1 g of a white crystal wereobtained. The resultant was identified as the intermediate-9′ by FD-MSanalysis.

Synthesis Example 33 Synthesis of Intermediate-10′

Under a nitrogen atmosphere, 150 g of dibenzofuran and 1 l of aceticacid were loaded into a 300-ml three-necked flask, and then the contentswere dissolved under heat. 188 Grams of bromine were added dropwise tothe solution. After that, the mixture was stirred for 20 hours under aircooling. The precipitated crystal was separated by filtration, and wasthen sequentially washed with acetic acid and water. The washed crystalwas dried under reduced pressure. The resultant crystal was purified bydistillation under reduced pressure, and was then repeatedlyrecrystallized with methanol several times. Thus, 66.8 g of2-bromodibenzofuran were obtained.

Under an argon atmosphere, 24.7 g of 2-bromodibenzofuran and 400 ml ofanhydrous THF were loaded into a 1,000-ml three-necked flask, and then63 ml of a solution of n-butyllithium in hexane having a concentrationof 1.6 M were added to the mixture during the stirring of the mixture at−40° C. The reaction solution was stirred for 1 hour while being heatedto 0° C. The reaction solution was cooled to −78° C. again, and then asolution of 26.0 g of trimethyl borate in 50 ml of dry THF was droppedto the solution. The reaction solution was stirred at room temperaturefor 5 hours. 200 milliliters of 1N hydrochloric acid were added to thesolution, and then the mixture was stirred for 1 hour. After that, theaqueous layer was removed. The organic layer was dried with magnesiumsulfate, and then the solvent was removed by distillation under reducedpressure. The resultant solid was washed with toluene. Thus, 15.2 g ofdibenzofuran-2-boronic acid were obtained.

Synthesis Example 34 Synthesis of Intermediate-11′

A reaction was performed in the same manner as in Synthesis Example 31except that 22.3 g of the intermediate-10′ were used instead of theintermediate-7′. Thus, 19.4 g of a white powder were obtained. Thepowder was identified as the intermediate-1′ by FD-MS analysis.

Synthesis Example 35 Synthesis of Intermediate-12′

A reaction was performed in the same manner as in Synthesis Example 31except that: 35.9 g of the Intermediate-1′ were used instead of4-iodobromobenzene; and 22.3 g of the intermediate-10′ were used insteadof the intermediate-7′. Thus, 28.7 g of a white powder were obtained.The powder was identified as the intermediate-12′ by FD-MS analysis.

Synthesis Example 36 Synthesis of Intermediate-13′

A reaction was performed in the same manner as in Synthesis Example 31except that: 39.9 g of the Intermediate-3′ were used instead of4-iodobromobenzene; and 22.3 g of the intermediate-10′ were used insteadof the intermediate-7′. Thus, 28.6 g of a white powder were obtained.The powder was identified as the intermediate-13′ by FD-MS analysis.

Synthesis Example 37 Synthesis of Intermediate-14′

A reaction was performed in the same manner as in Synthesis Example 31except that 22.3 g of dibenzofuran-4-boronic acid were used instead ofthe intermediate-7′. Thus, 25.9 g of a white powder were obtained. Thepowder was identified as the intermediate-14′ by FD-MS analysis.

Synthesis Example 38 Synthesis of Intermediate-15′

A reaction was performed in the same manner as in Synthesis Example 31except that: 35.9 g of the intermediate-1′ were used instead of4-iodobromobenzene; and 22.3 g of dibenzofuran-4-boronic acid were usedinstead of the intermediate-7′. Thus, 31.9 g of a white powder wereobtained. The powder was identified as the intermediate-15′ by FD-MSanalysis.

Synthesis Example 39 Synthesis of Intermediate-16′

A reaction was performed in the same manner as in Synthesis Example 31except that: 39.9 g of the intermediate-3′ were used instead of4-iodobromobenzene; and 22.3 g of dibenzofuran-4-boronic acid were usedinstead of the intermediate-7′. Thus, 35.7 g of a white powder wereobtained. The powder was identified as the intermediate-16′ by FD-MSanalysis.

Synthesis Example 40 Synthesis of Intermediate-17′

Under an argon atmosphere, 120.0 g of 1-bromo-3-fluoro-4-iodobenzene,72.7 g of 2-methoxyphenyl boronic acid, and 9.2 g oftetrakis(triphenylphosphine)palladium, 1,000 ml of toluene, and 500 mlof an aqueous solution of sodium carbonate having a concentration of 2 Mwere loaded into a 2,000-ml three-necked flask, and then the mixture washeated for 10 hours while being refluxed.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 89.6 g of a whitecrystal of 4-bromo-2-fluoro-2′-methoxybiphenyl were obtained.

Under an argon atmosphere, 89.6 g of 4-bromo-2-fluoro-2′-methoxybiphenyland 900 ml of dichloromethane were loaded into a 2,000-ml three-neckedflask, and then the mixture was stirred under ice cooling. 95.9 Grams ofboron tribromide were added dropwise to the mixture, and then the wholewas stirred at room temperature for 12 hours.

After the completion of the reaction, 200 ml of water were added to theresultant, and then the mixture was stirred for 1 hour. After that, theaqueous layer was removed. The organic layer was dried with magnesiumsulfate, and was then concentrated. The residue was purified by silicagel column chromatography. Thus, 68.1 g of a white crystal of4-bromo-2-fluoro-2′-hydroxybiphenyl were obtained.

68.1 Grams of 4-bromo-2-fluoro-2′-hydroxybiphenyl, 70.4 g of potassiumcarbonate, and 1,200 ml of N-methyl pyrrolidone were loaded into a2,000-ml three-necked flask, and then the mixture was stirred at 180° C.for 3 hours.

After the completion of the reaction, water was added to the resultant,and then extraction with toluene was performed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue wasrecrystallized from toluene so as to be purified. Thus, 44.2 g of awhite crystal of 3-bromodibenzofuran were obtained.

Under an argon atmosphere, 34.2 g of 3-bromodibenzofuran, 26.0 g of4-chlorophenyl boronic acid, 3.2 g oftetrakis(triphenylphosphine)palladium, 350 ml of toluene, and 170 ml ofan aqueous solution of sodium carbonate having a concentration of 2 Mwere loaded into a 1,000-ml three-necked flask, and then the mixture washeated for 12 hours while being refluxed.

Immediately after the completion of the reaction, the resultant wasfiltrated, and then the aqueous layer was removed. The organic layer wasdried with sodium sulfate, and was then concentrated. The residue waspurified by silica gel column chromatography. Thus, 23.1 g of a whitecrystal were obtained. The crystal was identified as theintermediate-17′ by FD-MS analysis.

Synthesis Example 41 Synthesis of Intermediate-18′

Under an argon atmosphere, 7.0 g of acetamide, 45.8 g of theintermediate-2, 6.8 g of copper(I) iodide, 6.3 g ofN,N′-dimethylethylenediamine, 51 g of tripotassium phosphate, and 300 mlof xylene were loaded into a 500-ml three-necked flask, and then themixture was subjected to a reaction at 140° C. for 36 hours. Afterhaving been cooled, the resultant was filtrated and washed with toluene.The washed product was further washed with water and methanol, and wasthen dried. Thus, 19 g of a pale yellow powder were obtained. The powderwas identified as the intermediate-18′ by FD-MS analysis.

Synthesis Example 42 Synthesis of Intermediate-19′

19.0 Grams of the intermediate-18′, 26 g of potassium hydroxide, 28 mlof ion-exchanged water, 39 ml of xylene, and 77 ml of ethanol wereloaded into a 300-ml three-necked flask, and then the mixture was heatedfor 36 hours while being refluxed. After the completion of the reaction,the resultant was extracted with toluene and dried with magnesiumsulfate. The dried product was concentrated under reduced pressure, andthen the resultant coarse product was subjected to column purification.The purified product was recrystallized with toluene, and then therecrystallized product was taken by filtration. After that, theresultant was dried. Thus, 15.8 g of the intermediate-19′ were obtainedas a white powder.

Synthesis Example 43 Synthesis of Intermediate-20′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 15 g of the intermediate-18′ were used instead ofacetamide and 26 g of 4-bromo-p-terphenyl were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 15.5 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-20′ by FD-MS analysis.

Synthesis Example 44 Synthesis of Intermediate-21′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 15 g of the intermediate-18′ were used instead ofacetamide and 29 g of intermediate-5′ were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 17.5 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-21′ by FD-MS analysis.

Synthesis Example 45 Synthesis of Intermediate-22′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 15 g of the intermediate-18′ were used instead ofacetamide and 29 g of intermediate-4′ were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 18.5 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-22′ by FD-MS analysis.

Synthesis Example 46 Synthesis of Intermediate-23′

A reaction was performed in the same manner as in Synthesis Example 41except that 29 g of the intermediate-4′ were used instead of theintermediate-2′. Thus, 20.2 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-23′ by FD-MS analysis.

Synthesis Example 47 Synthesis of Intermediate-24′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 20 g of the intermediate-23′ were used instead ofacetamide and 26 g of 4-bromo-p-terphenyl were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 19.8 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-24′ by FD-MS analysis.

Synthesis Example 48 Synthesis of Intermediate-25′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 15 g of the intermediate-18′ were used instead ofacetamide and 27 g of intermediate-14′ were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 17.3 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-25′ by FD-MS analysis.

Synthesis Example 49 Synthesis of Intermediate-26′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 15 g of the intermediate-18′ were used instead ofacetamide and 27 g of intermediate-11′ were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 17.8 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-26′ by FD-MS analysis.

Synthesis Example 50 Synthesis of Intermediate-27′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 15 g of the intermediate-18′ were used instead ofacetamide and 33 g of intermediate-9′ were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 20.3 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-27′ by FD-MS analysis.

Synthesis Example 51 Synthesis of Intermediate-28′

A reaction was performed in the same manner as in Synthesis Example 30except that 33 g of the intermediate-2′ were used instead of theintermediate-6′. Thus, 17 g of a white powder were obtained. The powderwas identified as the intermediate-28′ by EFD-MS analysis.

Synthesis Example 52 Synthesis of Intermediate-29′

A reaction was performed in the same manner as in Synthesis Example 31except that 17 g of the intermediate-28′ were used instead of theintermediate-7′. Thus, 20 g of a white powder were obtained. The powderwas identified as the intermediate-29′ by FD-MS analysis.

Synthesis Example 53 Synthesis of Intermediate-30′

A reaction was performed in the same manner as in Synthesis Example 41except that 20 g of the intermediate-29′ were used instead of theintermediate-2′. Thus, 12 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-30′ by FD-MS analysis.

Synthesis Example 54 Synthesis of Intermediate-31′

A reaction was performed in the same manner as in Synthesis Examples 41and 42 except that 12 g of the intermediate-30′ were used instead ofacetamide and 12.8 g of 4-bromobiphenyl were used instead of theintermediate-2′ upon performance of Synthesis Examples 41 and 42 in thestated order. Thus, 10.4 g of a pale yellow powder were obtained. Thepowder was identified as the intermediate-31′ by FD-MS analysis.

Shown below are the structures of the aromatic amine derivatives of thepresent invention produced in Examples-of-Synthesis 19 to 50 below andthe comparative compounds-1 and 2 used in Comparative Examples 1 and 2.

Example-of-Synthesis 19 Production of Aromatic Amine derivative (H-1′)

In a stream of argon, 6.5 g of the intermediate-14′, 8.8 g of theintermediate-20′, 2.6 g of t-butoxy sodium, 92 mg oftris(dibenzylideneacetone)dipalladium, 42 mg of tri-t-butylphosphine,and 100 ml of dry toluene were loaded into a 300-ml three-necked flask,and then the mixture was subjected to a reaction at 80° C. for 8 hours.

After having been cooled, the reaction product was poured into 500 ml ofwater, and then the mixture was subjected to celite filtration. Thefiltrate was extracted with toluene, and was then dried with anhydrousmagnesium sulfate. The dried product was concentrated under reducedpressure. The resultant coarse product was subjected to columnpurification, and was then recrystallized with toluene. The crystal wastaken by filtration, and was then dried. As a result, 8.2 g of a paleyellow powder were obtained. The powder was identified as aromatic aminederivative (H-1′) by FD-MS analysis.

Example-of-Synthesis 20 Production of Aromatic Amine Derivative (H-2′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 8.8 g of the intermediate-21′ were used instead of theintermediate-20′. Thus, 7.8 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-2′) by FD-MSanalysis.

Example-of-Synthesis 21 Production of Aromatic Amine Derivative (H-3′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 8.0 g of the intermediate-15′ were used instead of theintermediate-14′. Thus, 9.2 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-3′) by FD-MSanalysis.

Example-of-Synthesis 22 Production of Aromatic Amine Derivative (H-4′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-15′ were used instead of theintermediate-14′; and 9.6 g of the intermediate-22′ were used instead ofthe intermediate-20′. Thus, 9.4 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-4′) byFD-MS analysis.

Example-of-Synthesis 23 Production of Aromatic Amine Derivative (H-5′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 8.8 g of the intermediate-16′ were used instead of theintermediate-14′. Thus, 9.5 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-5′) by FD-MSanalysis.

Example-of-Synthesis 24 Production of Aromatic Amine Derivative (H-6′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 10.3 g of the intermediate-24′ were used instead of theintermediate-20′. Thus, 8.3 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-6′) by FD-MSanalysis.

Example-of-Synthesis 25 Production of Aromatic Amine Derivative (H-7′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 6.5 g of the intermediate-11′ were used instead of theintermediate-14′. Thus, 7.9 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-7′) by FD-MSanalysis.

Example-of-Synthesis 26 Production of Aromatic Amine Derivative (H-8′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 6.5 g of the intermediate-11′ were used instead of theintermediate-14′; and 8.8 g of the intermediate-21′ were used instead ofthe intermediate-20′. Thus, 8.2 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-8′) byFD-MS analysis.

Example-of-Synthesis 27 Production of Aromatic Amine Derivative (H-9′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 8.0 g of the intermediate-12′ were used instead of theintermediate-14′. Thus, 8.9 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-9′) by FD-MSanalysis.

Example-of-Synthesis 28 Production of Aromatic Amine Derivative (H-10′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 6.5 g of the intermediate-11′ were used instead of theintermediate-14′; and 9.6 g of the intermediate-22′ were used instead ofthe intermediate-20′. Thus, 9.3 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-10′) byFD-MS analysis.

Example-of-Synthesis 29 Production of Aromatic Amine Derivative (H-11′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 8.8 g of the intermediate-13′ were used instead of theintermediate-14′. Thus, 9.4 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-1′) by FD-MSanalysis.

Example-of-Synthesis 30 Production of Aromatic Amine Derivative (H-12′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 6.5 g of the intermediate-11′ were used instead of theintermediate-14′; and 10.3 g of the intermediate-24′ were used insteadof the intermediate-20′. Thus, 9.0 g of a pale yellow powder wereobtained. The powder was identified as the aromatic amine derivative(H-12′) by FD-MS analysis.

Example-of-Synthesis 31 Production of Aromatic Amine Derivative (H-13′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 5.6 g of the intermediate-17′ were used instead of theintermediate-14′. Thus, 8.3 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-13′) by FD-MSanalysis.

Example-of-Synthesis 32 Production of Aromatic Amine Derivative (H-14′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 5.6 g of the intermediate-17′ were used instead of theintermediate-14′; and 8.8 g of the intermediate-21′ were used instead ofthe intermediate-20′. Thus, 8.1 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-14′) byFD-MS analysis.

Example-of-Synthesis 33 Production of Aromatic Amine Derivative (H-15′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 5.6 g of the intermediate-17′ were used instead of theintermediate-14′; and 9.6 g of the intermediate-22′ were used instead ofthe intermediate-20′. Thus, 9.7 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-15′) byFD-MS analysis.

Example-of-Synthesis 34 Production of Aromatic Amine Derivative (H-16′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 5.6 g of the intermediate-17′ were used instead of theintermediate-14′; and 10.3 g of the intermediate-24′ were used insteadof the intermediate-20′. Thus, 9.5 g of a pale yellow powder wereobtained. The powder was identified as the aromatic amine derivative(H-16′) by FD-MS analysis.

Example-of-Synthesis 35 Production of Aromatic Amine Derivative (H-17′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-8′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-25′ were used instead ofthe intermediate-20′. Thus, 9.2 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-17′) byFD-MS analysis.

Example-of-Synthesis 36 Production of Aromatic Amine Derivative (H-18′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-9′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-25′ were used instead ofthe intermediate-20′. Thus, 8.8 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-18′) byFD-MS analysis.

Example-of-Synthesis 37 Production of Aromatic Amine Derivative (H-19′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-8′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-26′ were used instead ofthe intermediate-20′. Thus, 9.0 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-19′) byFD-MS analysis.

Example-of-Synthesis 38 Production of Aromatic Amine Derivative (H-20′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-9′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-26′ were used instead ofthe intermediate-20′. Thus, 9.7 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-20′) byFD-MS analysis.

Example-of-Synthesis 39 Production of Aromatic Amine Derivative (H-21′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-15′ were used instead of theintermediate-14′; and 10.5 g of the intermediate-27′ were used insteadof the intermediate-20′. Thus, 10.5 g of a pale yellow powder wereobtained. The powder was identified as the aromatic amine derivative(H-21′) by FD-MS analysis.

Example-of-Synthesis 40 Production of Aromatic Amine Derivative (H-22′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.8 g of the intermediate-16′ were used instead of theintermediate-14′; and 10.5 g of the intermediate-27′ were used insteadof the intermediate-20′. Thus, 9.5 g of a pale yellow powder wereobtained. The powder was identified as the aromatic amine derivative(H-22′) by FD-MS analysis.

Example-of-Synthesis 41 Production of Aromatic Amine Derivative (H-23′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 6.5 g of the intermediate-11′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-25′ were used instead ofthe intermediate-20′. Thus, 8.3 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-23′) byFD-MS analysis.

Example-of-Synthesis 42 Production of Aromatic Amine Derivative (H-24′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 9.0 g of the intermediate-25′ were used instead of theintermediate-20′. Thus, 8.1 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-24′) by FD-MSanalysis.

Example-of-Synthesis 43 Production of Aromatic Amine Derivative (H-25′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 6.5 g of the intermediate-11′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-26′ were used instead ofthe intermediate-20′. Thus, 8.7 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-25′) byFD-MS analysis.

Example-of-Synthesis 44 Production of Aromatic Amine Derivative (H-26′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-12′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-25′ were used instead ofthe intermediate-20′. Thus, 9.4 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-26′) byFD-MS analysis.

Example-of-Synthesis 45 Production of Aromatic Amine Derivative (H-27′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-15′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-25′ were used instead ofthe intermediate-20′. Thus, 9.0 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-27′) byFD-MS analysis.

Example-of-Synthesis 46 Production of Aromatic Amine Derivative (H-28′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-12′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-26′ were used instead ofthe intermediate-20′. Thus, 9.5 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-28′) byFD-MS analysis.

Example-of-Synthesis 47 Production of Aromatic Amine Derivative (H-29′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.0 g of the intermediate-15′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-26′ were used instead ofthe intermediate-20′. Thus, 8.8 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-29′) byFD-MS analysis.

Example-of-Synthesis 48 Production of Aromatic Amine Derivative (H-30′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.8 g of the intermediate-13′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-25′ were used instead ofthe intermediate-20′. Thus, 10.0 g of a pale yellow powder wereobtained. The powder was identified as the aromatic amine derivative(H-30′) by FD-MS analysis.

Example-of-Synthesis 49 Production of Aromatic Amine Derivative (H-31′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that: 8.8 g of the intermediate-16′ were used instead of theintermediate-14′; and 9.0 g of the intermediate-26′ were used instead ofthe intermediate-20′. Thus, 9.7 g of a pale yellow powder were obtained.The powder was identified as the aromatic amine derivative (H-31′) byFD-MS analysis.

Example-of-Synthesis 50 Production of Aromatic Amine Derivative (H-32′)

A reaction was performed in the same manner as in Example-of-Synthesis19 except that 8.8 g of the intermediate-31′ were used instead of theintermediate-20′. Thus, 8.5 g of a pale yellow powder were obtained. Thepowder was identified as the aromatic amine derivative (H-32′) by FD-MSanalysis.

Example 1 Production of Organic EL Device

A glass substrate with an ITO transparent electrode measuring mm wide by75 mm long by 1.1 mm thick (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes.After that, the substrate was subjected to UV ozone cleaning for 30minutes.

The glass substrate with the transparent electrode line after thecleaning was mounted on a substrate holder of a vacuum vapor depositiondevice. First, the following compound H232 was deposited from vapor onthe surface on the side where the transparent electrode line was formedso as to cover the transparent electrode. Then, the H232 film having athickness of 60 nm was formed as the hole injecting layer. The aromaticamine derivative (H-1′) obtained in Example-of-Synthesis 19 wasdeposited from vapor and formed into a hole transporting layer having athickness of 20 nm on the H232 film. Further, the following compound EM1was deposited from vapor and formed into a light emitting layer having athickness of 40 nm. Simultaneously with this formation, the followingamine compound D1 having a styryl group, as a light emitting molecule,was deposited from vapor in such a manner that a weight ratio betweenthe compound EM1 and the amine compound D1 was 40:2.

The following Alq was formed into a film having a thickness of 10 nm onthe resultant film. The film functions as an electron injecting layer.After that, Li serving as a reducing dopant (Li source: manufactured bySAES Getters) and the following Alq were subjected to co-vapordeposition. Thus, an Alq:Li film (having a thickness of 10 nm) wasformed as an electron injecting layer (cathode). Metal Al was depositedfrom vapor onto the Alq:Li film to form a metal cathode. Thus, anorganic EL device was formed.

The current efficiency of the resultant organic EL device was measured,and the luminescent color of the device was observed. It should be notedthat a current efficiency at 10 mA/cm² was calculated by measuring aluminance by using a spectral radiance meter “CS1000” (manufactured byKonica Minolta Sensing, Inc.). Further, the half lifetime of its lightemission when the device was driven with a DC constant current at aninitial luminance of 5,000 cd/m² and room temperature was measured.Table 2 shows the results.

Examples 2 to 12 Production of Organic EL Device

Each organic EL device was produced in the same manner as in Example 1except that the respective aromatic amine derivatives shown in Table 2were used as hole transporting materials instead of the aromatic aminederivative (H-1′).

In the same manner as in Example 1, the current efficiency of theresultant organic EL device was measured, the luminescent color of thedevice was observed, and the half lifetime of its light emission whenthe device was driven with a DC constant current at an initial luminanceof 5,000 cd/m² and room temperature was measured. Table 2 shows theresults.

Example 13 Production of Organic EL Device

An organic EL device was produced in the same manner as in Example 1except that the following arylamine compound D2 was used instead of theamine compound D1 having a styryl group.

In addition, in the same manner as in Example 1, the current efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of its light emissionwhen the device was driven with a DC constant current at an initialluminance of 5,000 cd/m² and room temperature was measured. Table 2shows the results.

Example 14 Production of Organic EL Device

An organic EL device was produced in the same manner as in Example 1except that the following imidazole compound (ET1) was used as anelectron transporting material instead of Alq.

In addition, in the same manner as in Example 1, the current efficiencyof the resultant organic EL device was measured, the luminescent colorof the device was observed, and the half lifetime of its light emissionwhen the device was driven with a DC constant current at an initialluminance of 5,000 cd/m² and room temperature was measured. Table 2shows the results.

Example 15 Production of Organic EL Device

An organic EL device was produced in the same manner as in Example 1except that the following acceptor compound (C-1) was formed into a filmhaving a thickness of 10 nm instead of H232, and then the aromatic aminederivative (H-1′) was formed into a film having a thickness of 70 nm.

In addition, in the same manner as in Example 1, the current efficiencyof the resultant organic EL device was measured, its luminescent colorwas observed, and the half lifetime of its light emission when thedevice was driven with a DC constant current at an initial luminance of5,000 cd/m² and room temperature was measured. Table 2 shows theresults.

Comparative Examples 1 and 2

Organic EL devices were each produced in the same manner as in Example 1except that the comparative compound-1 or 2 shown in Table 2 was used asa hole transporting material instead of the compound H1.

In addition, in the same manner as in Example 1, the current efficiencyof each of the resultant organic EL devices was measured, itsluminescent color was observed, and the half lifetime of its lightemission when the device was driven with a DC constant current at aninitial luminance of 5,000 cd/m² and room temperature was measured.Table 2 shows the results.

Comparative Example 3

An organic EL device was produced in the same manner as in Example 13except that the comparative compound-1 was used as a hole transportingmaterial instead of the aromatic amine derivative (H-1′).

In addition, in the same manner as in Example 1, the current efficiencyof the resultant organic EL device was measured, its luminescent colorwas observed, and the half lifetime of its light emission when thedevice was driven with a DC constant current at an initial luminance of5,000 cd/m² and room temperature was measured. Table 2 shows theresults.

Comparative Example 4

An organic EL device was produced in the same manner as in Example 14except that the comparative compound-1 was used as a hole transportingmaterial instead of the aromatic amine derivative (H-1′).

In addition, in the same manner as in Example 1, the current efficiencyof the resultant organic EL device was measured, its luminescent colorwas observed, and the half lifetime of its light emission when thedevice was driven with a DC constant current at an initial luminance of5,000 cd/m² and room temperature was measured. Table 2 shows theresults.

Comparative Example 5

An organic EL device was produced in the same manner as in Example 15except that the comparative compound-1 was used as a hole transportingmaterial instead of the aromatic amine derivative (H-1′).

In addition, in the same manner as in Example 1, the current efficiencyof the resultant organic EL device was measured, its luminescent colorwas observed, and the half lifetime of its light emission when thedevice was driven with a DC constant current at an initial luminance of5,000 cd/m² and room temperature was measured. Table 2 shows theresults.

TABLE 2 Driving Half Hole transporting Luminescent voltage lifetimematerial color (V) (h) Example  1 H-1′  blue 7.1 400  2 H-6′  blue 7.0410  3 H-7′  blue 6.8 350  4 H-12′ blue 6.8 360  5 H-13′ blue 6.7 350  6H-16′ blue 6.7 360  7 H-17′ blue 6.8 380  8 H-18′ blue 6.9 400  9 H-19′blue 6.6 330 10 H-23′ blue 6.8 350 11 H-24′ blue 7.0 400 12 H-25′ blue6.7 310 13 H-1′  blue 7.2 390 14 H-1′  blue 6.8 380 15 H-1′  blue 6.8320 Compara-  1 Comparative blue 7.8 160 tive compound-1 Example  2Comparative blue 8.0 130 compound-2  3 Comparative blue 7.9 130compound-1  4 Comparative blue 7.2 150 compound-1  5 Comparative blue7.2 90 compound-1

As is apparent from the results of Table 2, an organic EL device usingthe aromatic amine derivative of the present invention is driven at areduced voltage and has a long half lifetime as compared with an organicEL device using an aromatic amine derivative for comparison.

INDUSTRIAL APPLICABILITY

The utilization of the aromatic amine derivative of the presentinvention as a material for an organic EL device (especially a holetransporting material) provides the following organic EL device. Theorganic EL device has high luminous efficiency and a long lifetime, andis driven at a reduced voltage. Accordingly, the organic EL device ofthe present invention can be utilized in, for example, flat luminousbodies such as the flat panel display of a wall television, lightsources for the backlights, meters, and the like of a copying machine, aprinter, and a liquid crystal display, display boards, andidentification lamps.

In addition, the material of the present invention is useful not only inthe field of an organic EL device but also in the fields of, forexample, an electrophotographic photosensitive member, a photoelectricconverter, a solar cell, and an image sensor.

1. An aromatic amine derivative of formula (I):

wherein: Ar^(a) is of formula (II):

L^(a) is a single bond, or a substituted or unsubstituted arylene grouphaving 6 to 50 ring carbon atoms; R¹ and R² each are a linear orbranched alkyl group having 1 to 50 carbon atoms, or an aryl grouphaving 6 to 50 ring carbon atoms; R³ and R⁴ each independently are alinear or branched alkyl group having 1 to 50 carbon atoms, a linear orbranched alkenyl group having 3 to 50 carbon atoms, a cycloalkyl grouphaving 3 to 50 ring carbon atoms, an aryl group having 6 to 50 ringcarbon atoms, a heteroaryl group having 5 to 50 ring atoms, atriarylalkyl group having aryl groups each having 6 to 50 ring carbonatoms, a trialkylsilyl group having alkyl groups each having 1 to 50carbon atoms, a triarylsilyl group having aryl groups each having 6 to50 ring carbon atoms, an alkylarylsilyl group having an alkyl grouphaving 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbonatoms, a halogen atom, or a cyano group, such that a plurality of R³'sor R⁴'s are optionally adjacent to each other, or R³ and R⁴ may bebonded to each other to form a ring; o is an integer of 0 to 3; p is aninteger of 0 to 4; Ar^(b) is of formula (III):

X is NR^(a), an oxygen atom, or a sulfur atom; R^(a) is a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms, or atriarylalkyl group having substituted or unsubstituted aryl groups eachhaving 6 to 50 ring carbon atoms; R⁵, R⁶, and R⁷ each independently area linear or branched alkyl group having 1 to 50 carbon atoms, a linearor branched alkenyl group having 3 to 50 carbon atoms, a cycloalkylgroup having 3 to 50 ring carbon atoms, an aryl group having 6 to 50ring carbon atoms, a heteroaryl group having 6 to 50 ring atoms, atriarylalkyl group having aryl groups each having 6 to 50 ring carbonatoms, a trialkylsilyl group having alkyl groups each having 1 to 50carbon atoms, a triarylsilyl group having aryl groups each having 6 to50 ring carbon atoms, an alkylarylsilyl group having an alkyl grouphaving 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbonatoms, a halogen atom, or a cyano group, such that a plurality of R⁵'s,R⁶'s, or R⁷'s adjacent to each other, or R⁵ and R⁶ may be bonded to eachother to form a ring; n is an integer of 2 to 4 when X is NR^(a), and isan integer of 0 to 4 when X is an oxygen atom or a sulfur atom; when nis an integer of 2 to 4, R⁷'s on different benzene rings may beidentical to or different from each other, and respective R⁷'s presenton benzene rings adjacent to each other may be bonded to each other toform a ring; q is an integer of 0 to 3; r and s each independently arean integer of 0 to 4; when n is an integer of 2 to 4, s's that specifythe numbers of R⁷'s on different benzene rings may have the same valueor may have different values; and Ar^(c) is a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms, or is offormula (III).
 2. The aromatic amine derivative of claim 1, wherein:Ar^(a) is of formula (II′):

L^(a) is a single bond, or a substituted or unsubstituted arylene grouphaving 6 to 50 ring carbon atoms; R¹ and R² each are a linear orbranched alkyl group having 1 to 50 carbon atoms, or an aryl grouphaving 6 to 50 ring carbon atoms; R³ and R⁴ each independently are alinear or branched alkyl group having 1 to 50 carbon atoms, a linear orbranched alkenyl group having 3 to 50 carbon atoms, a cycloalkyl grouphaving 3 to 50 ring carbon atoms, an aryl group having 6 to 50 ringcarbon atoms, a heteroaryl group having 5 to 50 ring atoms, atriarylalkyl group having aryl groups each having 6 to 50 ring carbonatoms, a trialkylsilyl group having alkyl groups each having 1 to 50carbon atoms, a triarylsilyl group having aryl groups each having 6 to50 ring carbon atoms, an alkylarylsilyl group having an alkyl grouphaving 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbonatoms, a halogen atom, or a cyano group, such that a plurality of R³'sor R⁴'s are optionally adjacent to each other, or R³ and R⁴ may bebonded to each other to form a ring; o is an integer of 0 to 3; p is aninteger of 0 to
 4. 3. The aromatic amine derivative of claim 1, whereinL^(a) is a single bond.
 4. The aromatic amine derivative of claim 1,wherein R¹ and R² each are a linear or branched alkyl group having 1 to10 carbon atoms.
 5. The aromatic amine derivative of claim 1, wherein R¹and R² each are a methyl group.
 6. The aromatic amine derivative ofclaim 1, wherein: Ar^(b) is of formula (III′):

X is NR^(a), an oxygen atom, or a sulfur atom; R^(a) is a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms, or atriarylalkyl group having substituted or unsubstituted aryl groups eachhaving 6 to 50 ring carbon atoms; R⁵, R⁶, and R⁷ each independently area linear or branched alkyl group having 1 to 50 carbon atoms, a linearor branched alkenyl group having 3 to 50 carbon atoms, a cycloalkylgroup having 3 to 50 ring carbon atoms, an aryl group having 6 to 50ring carbon atoms, a heteroaryl group having 6 to 50 ring atoms, atriarylalkyl group having aryl groups each having 6 to 50 ring carbonatoms, a trialkylsilyl group having alkyl groups each having 1 to 50carbon atoms, a triarylsilyl group having aryl groups each having 6 to50 ring carbon atoms, an alkylarylsilyl group having an alkyl grouphaving 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbonatoms, a halogen atom, or a cyano group, such that a plurality of R⁵'s,R⁶'s, or R⁷'s adjacent to each other, or R⁵ and R⁶ may be bonded to eachother to form a ring; n is an integer of 2 to 4 when X is NR^(a), and isan integer of 0 to 4 when X is an oxygen atom or a sulfur atom; when nis an integer of 2 to 4, R⁷'s on different benzene rings may beidentical to or different from each other, and respective R⁷'s presenton benzene rings adjacent to each other may be bonded to each other toform a ring; q is an integer of 0 to 3; r and s each independently arean integer of 0 to 4; when n is an integer of 2 to 4, s's that specifythe numbers of R⁷'s on different benzene rings may have the same valueor may have different values; and Ar^(c) is a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms, or is offormula (III′).
 7. The aromatic amine derivative of claim 1, whereinAr^(b) is of any one of formulae (III-1) to (III-6):

wherein X is NR^(a), an oxygen atom, or a sulfur atom; R⁵, R⁶, and R⁷each independently are a linear or branched alkyl group having 1 to 50carbon atoms, a linear or branched alkenyl group having 3 to 50 carbonatoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an arylgroup having 6 to 50 ring carbon atoms, a heteroaryl group having 6 to50 ring atoms, a triarylalkyl group having aryl groups each having 6 to50 ring carbon atoms, a trialkylsilyl group having alkyl groups eachhaving 1 to 50 carbon atoms, a triarylsilyl group having aryl groupseach having 6 to 50 ring carbon atoms, an alkylarylsilyl group having analkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50ring carbon atoms, a halogen atom, or a cyano group, such that aplurality of R⁵'s, R⁶'s, or R⁷'s adjacent to each other, or R⁵ and R⁶may be bonded to each other to form a ring; q is an integer of 0 to 3; rand s each independently are an integer of 0 to 4; and wherein R⁷'s ors's described in plurality may be identical to or different from eachother.
 8. The aromatic amine derivative of claim 1, wherein Ar^(b) is ofany one of formulae (III-2), (III-3), and (III-6):

wherein X is NR^(a), an oxygen atom, or a sulfur atom; R⁵, R⁶, and R⁷each independently are a linear or branched alkyl group having 1 to 50carbon atoms, a linear or branched alkenyl group having 3 to 50 carbonatoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an arylgroup having 6 to 50 ring carbon atoms, a heteroaryl group having 6 to50 ring atoms, a triarylalkyl group having aryl groups each having 6 to50 ring carbon atoms, a trialkylsilyl group having alkyl groups eachhaving 1 to 50 carbon atoms, a triarylsilyl group having aryl groupseach having 6 to 50 ring carbon atoms, an alkylarylsilyl group having analkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50ring carbon atoms, a halogen atom, or a cyano group, such that aplurality of R⁵'s, R⁶'s, or R⁷'s adjacent to each other, or R⁵ and R⁶may be bonded to each other to form a ring; q is an integer of 0 to 3; rand s each independently are an integer of 0 to 4; and wherein R⁷'s ors's described in plurality may be identical to or different from eachother.
 9. The aromatic amine derivative of claim 1, wherein Ar^(c) is offormula (IV):

wherein: R⁸ and R⁹ each are a halogen atom, a linear or branched alkylgroup having 1 to 50 carbon atoms, a linear or branched alkenyl grouphaving 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbonatoms, or a heteroaryl group having 5 to 50 ring atoms, a plurality ofR⁸'s or R⁹'s adjacent to each other, or R⁸ and R⁹ may be bonded to eachother to form a ring, and an oxygen atom or a nitrogen atom may bepresent in the ring; n′ is an integer of 0 to 3; t is an integer of 0 to4; u is an integer of 0 to 5, and when n′ is 2 or 3, R⁸'s on differentbenzene rings may be identical to or different from each other.
 10. Thearomatic amine derivative of claim 9, wherein n′ in formula (IV) is 2 or3.
 11. The aromatic amine derivative of claim 1, wherein Ar^(c) isselected from the group consisting of a biphenylyl group, a terphenylylgroup, a quaterphenylyl group, a naphthyl group, an anthryl group, afluorenyl group, a phenanthryl group, a dibenzofuranyl group, acarbazolyl group, and a dibenzothiophenyl group.
 12. The aromatic aminederivative of claim 1, wherein Ar^(c) is a terphenylyl group or aquaterphenylyl group.
 13. The aromatic amine derivative of claim 1,wherein Ar^(c) is of formula (III).
 14. The aromatic amine derivative ofclaim 13, wherein Ar^(c) is of formula (III′):

wherein: X is NR^(a), an oxygen atom, or a sulfur atom; R⁵, R⁶, and R⁷each independently are a linear or branched alkyl group having 1 to 50carbon atoms, a linear or branched alkenyl group having 3 to 50 carbonatoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an arylgroup having 6 to 50 ring carbon atoms, a heteroaryl group having 6 to50 ring atoms, a triarylalkyl group having aryl groups each having 6 to50 ring carbon atoms, a trialkylsilyl group having alkyl groups eachhaving 1 to 50 carbon atoms, a triarylsilyl group having aryl groupseach having 6 to 50 ring carbon atoms, an alkylarylsilyl group having analkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50ring carbon atoms, a halogen atom, or a cyano group, such that aplurality of R⁵'s, R⁶'s, or R⁷'s adjacent to each other, or R⁵ and R⁶may be bonded to each other to form a ring; n is an integer of 2 to 4when X is NR^(a), and is an integer of 0 to 4 when X is an oxygen atomor a sulfur atom; when n is an integer of 2 to 4, R⁷'s on differentbenzene rings may be identical to or different from each other, andrespective R⁷'s present on benzene rings adjacent to each other may bebonded to each other to form a ring; q is an integer of 0 to 3; r and seach independently are an integer of 0 to 4; when n is an integer of 2to 4, s's that specify the numbers of R⁷'s on different benzene ringsmay have the same value or may have different values.
 15. The aromaticamine derivative of claim 1, wherein X is NR^(a).
 16. The aromatic aminederivative of claim 1, wherein X is an oxygen atom or a sulfur atom. 17.An organic electroluminescence device, comprising an organic thin-filmlayer comprising a light emitting layer, wherein the organic thin-filmlayer is interposed between an anode and a cathode, and at least onelayer of the organic thin-film layer comprises the aromatic aminederivative of claim
 1. 18. The organic electroluminescence device ofclaim 17, comprising a hole injecting layer or a hole transporting layeras the organic thin-film layer, wherein the aromatic amine derivative ofclaim 1 is incorporated into the hole injecting layer or the holetransporting layer.
 19. The organic electroluminescence device of claim17, wherein a styrylamine compound and an arylamine compound areincorporated into the light emitting layer.
 20. The organicelectroluminescence device of claim 17, comprising an electrontransporting layer as the organic thin-film layer, wherein anitrogen-containing heterocyclic derivative of any one of formulae (1)to (3) is incorporated into the electron transporting layer:

wherein: Z¹, Z², and Z³ each independently is a nitrogen atom or acarbon atom; R¹¹ and R¹² each independently is a substituted orunsubstituted aryl group having 6 to 50 carbon atoms, a substituted orunsubstituted heteroaryl group having 3 to 50 carbon atoms, an alkylgroup having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbonatoms and substituted with a halogen atom, or an alkoxy group having 1to 20 carbon atoms; m is an integer of 0 to 5, such that when m is aninteger of 2 or more, a plurality of R¹¹'s may be identical to ordifferent from each other, and a plurality of R¹'s adjacent to eachother may be bonded to each other to form a substituted or unsubstitutedaromatic hydrocarbon ring; Ar¹ is a substituted or unsubstituted arylgroup having 6 to 50 carbon atoms, or a substituted or unsubstitutedheteroaryl group having 3 to 50 carbon atoms; Ar² is a hydrogen atom, analkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20carbon atoms and substituted with a halogen atom, an alkoxy group having1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6to 50 carbon atoms, or a substituted or unsubstituted heteroaryl grouphaving 3 to 50 carbon atoms, provided that one of Ar¹ and Ar² is asubstituted or unsubstituted fused ring group having 10 to 50 carbonatoms, or a substituted or unsubstituted heterofused ring group having 9to 50 ring atoms; Ar³ is a substituted or unsubstituted arylene grouphaving 6 to 50 carbon atoms, or a substituted or unsubstitutedheteroarylene group having 3 to 50 carbon atoms; and L¹, L², and L³ eachindependently are a single bond, a substituted or unsubstituted arylenegroup having 6 to 50 carbon atoms, a substituted or unsubstitutedheterofused ring group having 9 to 50 ring atoms, or a substituted orunsubstituted fluorenylene group.
 21. The organic electroluminescencedevice of claim 17, comprising at least a hole injecting layer as theorganic thin-film layer, wherein a compound of formula (A) isincorporated into the hole injecting layer:

wherein: R¹¹¹ to R¹¹⁶ each independently are a cyano group, —CONH₂, acarboxyl group, or —COOR¹¹⁷ and R¹¹⁷ is an alkyl group having 1 tocarbon atoms, or R¹¹¹ and R¹¹², R¹¹³ and R¹¹⁴, or R¹¹⁵ and R¹⁶ combinewith each other to are a group of —CO—O—CO—.
 22. The organicelectroluminescence device of claim 17, wherein the device emits bluishlight